# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_zhm632
_database_code_depnum_ccdc_archive 'CCDC 2159550'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2022-03-17 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_audit_creation_date             2020-10-22
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.25
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.7556(19)
_cell_length_b                   7.6524(7)
_cell_length_c                   15.3789(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.227(10)
_cell_angle_gamma                90
_cell_volume                     2431.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    149.97(10)
_cell_measurement_theta_max      29.0400
_cell_measurement_theta_min      2.8110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.789
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  59.00   1.00    5.00    --  -11.43  77.00 -90.00   65
  2  ω    -79.00   1.00   1.00    5.00    --  -11.43 -57.00   0.00   80
  3  ω    -16.00  51.00   1.00    5.00    --   12.05 -99.00-180.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0341999000
_diffrn_orient_matrix_UB_12      -0.0001859000
_diffrn_orient_matrix_UB_13      0.0191695000
_diffrn_orient_matrix_UB_21      0.0013555000
_diffrn_orient_matrix_UB_22      -0.0820918000
_diffrn_orient_matrix_UB_23      -0.0207503000
_diffrn_orient_matrix_UB_31      0.0027186000
_diffrn_orient_matrix_UB_32      0.0430661000
_diffrn_orient_matrix_UB_33      -0.0394607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1868
_reflns_number_total             2142
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.088
_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)+(0.0423P)²+1.7654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1010
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.15021(5) 0.57293(15) 0.53410(7) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.22448(5) 0.71213(13) 0.84043(7) 0.0229(3) Uani 1 1 d . . . . .
O3 O 0.39866(6) 0.54469(18) 1.02873(8) 0.0393(3) Uani 1 1 d . . . . .
O4 O 0.44974(5) 0.67382(19) 0.92316(9) 0.0411(3) Uani 1 1 d . . . . .
H4 H 0.445932 0.626188 0.968965 0.062 Uiso 1 1 calc R U . . .
C1 C 0.16978(7) 0.7146(2) 0.76545(10) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.10939(7) 0.7747(2) 0.76462(11) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.101788 0.818646 0.816702 0.033 Uiso 1 1 calc R U . . .
C3 C 0.06137(8) 0.7647(2) 0.68109(12) 0.0315(4) Uani 1 1 d . . . . .
H3 H 0.020011 0.803452 0.676785 0.038 Uiso 1 1 calc R U . . .
C4 C 0.07272(7) 0.6982(2) 0.60264(11) 0.0283(4) Uani 1 1 d . . . . .
H4A H 0.039033 0.693357 0.547705 0.034 Uiso 1 1 calc R U . . .
C5 C 0.13366(7) 0.6396(2) 0.60615(11) 0.0239(4) Uani 1 1 d . . . . .
C6 C 0.18358(7) 0.64889(19) 0.68942(10) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.25077(7) 0.6021(2) 0.72075(10) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.274239 0.553393 0.685573 0.026 Uiso 1 1 calc R U . . .
C8 C 0.27364(7) 0.64156(19) 0.81050(11) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.33747(7) 0.6288(2) 0.87987(11) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.34384(8) 0.5513(2) 0.96648(11) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.28784(8) 0.4725(2) 0.98878(12) 0.0346(4) Uani 1 1 d . . . . .
H11A H 0.303282 0.386274 1.035932 0.052 Uiso 1 1 calc R U . . .
H11B H 0.259187 0.418344 0.935021 0.052 Uiso 1 1 calc R U . . .
H11C H 0.265034 0.562211 1.009752 0.052 Uiso 1 1 calc R U . . .
C12 C 0.39332(8) 0.6870(2) 0.86173(12) 0.0290(4) Uani 1 1 d . . . . .
C13 C 0.39488(8) 0.7642(2) 0.77334(13) 0.0358(4) Uani 1 1 d . . . . .
H13A H 0.428716 0.849986 0.785126 0.054 Uiso 1 1 calc R U . . .
H13B H 0.354045 0.818728 0.743001 0.054 Uiso 1 1 calc R U . . .
H13C H 0.402902 0.673713 0.735043 0.054 Uiso 1 1 calc R U . . .
C14 C 0.09980(8) 0.5574(3) 0.44879(12) 0.0385(5) Uani 1 1 d . . . . .
H14A H 0.117196 0.510279 0.403573 0.058 Uiso 1 1 calc R U . . .
H14B H 0.081571 0.670580 0.429492 0.058 Uiso 1 1 calc R U . . .
H14C H 0.066723 0.480950 0.455930 0.058 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 C5 1.3663(19) . ?
O1 C14 1.428(2) . ?
O2 C1 1.3740(18) . ?
O2 C8 1.3982(17) . ?
O3 C10 1.2756(19) . ?
O4 H4 0.8200 . ?
O4 C12 1.298(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.389(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(2) . ?
C4 H4A 0.9300 . ?
C4 C5 1.384(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.434(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.347(2) . ?
C8 C9 1.466(2) . ?
C9 C10 1.425(2) . ?
C9 C12 1.402(2) . ?
C10 C11 1.492(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.492(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C5 O1 C14 117.05(12) . . ?
C1 O2 C8 106.25(11) . . ?
C12 O4 H4 109.5 . . ?
O2 C1 C2 125.52(14) . . ?
O2 C1 C6 110.06(12) . . ?
C2 C1 C6 124.42(14) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 C1 115.37(15) . . ?
C3 C2 H2 122.3 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.37(14) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 C3 120.58(15) . . ?
C5 C4 H4A 119.7 . . ?
O1 C5 C4 125.53(14) . . ?
O1 C5 C6 115.82(13) . . ?
C4 C5 C6 118.64(14) . . ?
C1 C6 C5 118.62(13) . . ?
C1 C6 C7 105.88(13) . . ?
C5 C6 C7 135.50(14) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 C6 107.41(13) . . ?
C8 C7 H7 126.3 . . ?
O2 C8 C9 115.72(13) . . ?
C7 C8 O2 110.40(13) . . ?
C7 C8 C9 133.86(14) . . ?
C10 C9 C8 120.08(14) . . ?
C12 C9 C8 121.11(15) . . ?
C12 C9 C10 118.78(14) . . ?
O3 C10 C9 120.86(15) . . ?
O3 C10 C11 116.77(15) . . ?
C9 C10 C11 122.37(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C9 120.78(16) . . ?
O4 C12 C13 114.08(14) . . ?
C9 C12 C13 125.13(15) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C5 C6 C1 -179.66(13) . . . . ?
O1 C5 C6 C7 -1.2(3) . . . . ?
O2 C1 C2 C3 179.92(14) . . . . ?
O2 C1 C6 C5 179.54(13) . . . . ?
O2 C1 C6 C7 0.64(17) . . . . ?
O2 C8 C9 C10 49.77(19) . . . . ?
O2 C8 C9 C12 -132.22(15) . . . . ?
C1 O2 C8 C7 0.18(16) . . . . ?
C1 O2 C8 C9 179.14(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C6 C7 C8 -0.52(17) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C6 C7 -179.80(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 O1 -179.79(15) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 179.29(16) . . . . ?
C5 C6 C7 C8 -179.14(17) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C7 C8 O2 0.22(17) . . . . ?
C6 C7 C8 C9 -178.49(16) . . . . ?
C7 C8 C9 C10 -131.58(19) . . . . ?
C7 C8 C9 C12 46.4(3) . . . . ?
C8 O2 C1 C2 179.94(15) . . . . ?
C8 O2 C1 C6 -0.52(16) . . . . ?
C8 C9 C10 O3 -177.52(14) . . . . ?
C8 C9 C10 C11 3.2(2) . . . . ?
C8 C9 C12 O4 -179.35(15) . . . . ?
C8 C9 C12 C13 -0.6(2) . . . . ?
C10 C9 C12 O4 -1.3(2) . . . . ?
C10 C9 C12 C13 177.47(15) . . . . ?
C12 C9 C10 O3 4.4(2) . . . . ?
C12 C9 C10 C11 -174.83(15) . . . . ?
C14 O1 C5 C4 -2.1(2) . . . . ?
C14 O1 C5 C6 178.35(14) . . . . ?

_olex2_date_sample_data_collection 2020-10-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.477
_oxdiff_exptl_absorpt_empirical_full_min 0.519
