# 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_201205e
_database_code_depnum_ccdc_archive 'CCDC 2049470'
loop_
_audit_author_name
_audit_author_address
'Qi Teng'
;Shandong University
China
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 O3'
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         CO
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5233(2)
_cell_length_b                   10.3088(3)
_cell_length_c                   12.0352(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1057.47(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.5780
_cell_measurement_theta_min      5.6270
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3520
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        66.949
_diffrn_reflns_theta_max         66.949
_diffrn_reflns_theta_min         5.651
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -38.00   1.00    0.10    --  -48.45 -62.00-135.00   31
  2  ω   -108.00 -73.00   1.00    0.10    --  -48.45 -62.00-135.00   35
  3  ω    -24.00  25.00   1.00    0.10    --  -48.45  19.00-180.00   49
  4  ω   -144.00 -99.00   1.00    0.50    --  -86.25-144.00  -7.00   45
  5  ω    -89.00 -63.00   1.00    0.50    --  -86.25-144.00  -7.00   26
  6  ω   -156.00 -74.00   1.00    0.50    --  -86.25-125.00-180.00   82
  7  ω    -41.00 -15.00   1.00    0.50    --  -86.25  38.00-120.00   26
  8  ω    -43.00 -13.00   1.00    0.50    --  -86.25  38.00  90.00   30
  9  ω     34.00  64.00   1.00    0.50    --  106.49 -57.00-180.00   30
 10  ω     35.00  69.00   1.00    0.50    --  106.49 -62.00-135.00   34
 11  ω     36.00  61.00   1.00    0.50    --  106.49 -58.00  35.00   25
 12  ω     40.00  66.00   1.00    0.50    --  106.49 -57.00 120.00   26
 13  ω    114.00 153.00   1.00    0.50    --  106.49  58.00 176.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1700367000
_diffrn_orient_matrix_UB_12      0.0283399000
_diffrn_orient_matrix_UB_13      0.0361647000
_diffrn_orient_matrix_UB_21      0.0603542000
_diffrn_orient_matrix_UB_22      -0.0992385000
_diffrn_orient_matrix_UB_23      -0.0855369000
_diffrn_orient_matrix_UB_31      0.0109425000
_diffrn_orient_matrix_UB_32      0.1080641000
_diffrn_orient_matrix_UB_33      -0.0880943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.768
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                1568
_reflns_number_total             1698
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.051
_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)+(0.0903P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1281
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.c Me refined as rotating group:
 C00E(H00E,H00F,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D)
2.e Idealised Me refined as rotating group:
 C00F(H00H,H00I,H00J)
;
_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
O001 O 0.9488(2) 0.39189(19) 0.5341(2) 0.0549(6) Uani 1 1 d . . . . .
O002 O 0.3790(3) 0.60517(19) 0.4696(2) 0.0537(6) Uani 1 1 d . . . . .
O003 O 0.7125(3) 0.2099(2) 0.67334(19) 0.0615(6) Uani 1 1 d . . . . .
C004 C 0.8176(3) 0.4353(2) 0.52145(19) 0.0381(6) Uani 1 1 d . . . . .
C005 C 0.5264(3) 0.4134(2) 0.47241(17) 0.0338(5) Uani 1 1 d . . . . .
H005 H 0.467255 0.358664 0.420668 0.041 Uiso 1 1 calc R U . . .
C006 C 0.4376(3) 0.4280(2) 0.5789(2) 0.0371(6) Uani 1 1 d . . . . .
C007 C 0.6783(3) 0.3450(2) 0.50677(18) 0.0348(6) Uani 1 1 d . . . . .
H007 H 0.703732 0.274952 0.454722 0.042 Uiso 1 1 calc R U . . .
C008 C 0.6359(3) 0.2892(2) 0.6229(2) 0.0391(6) Uani 1 1 d . . . . .
C009 C 0.4930(4) 0.3555(2) 0.6620(2) 0.0415(6) Uani 1 1 d . . . . .
C00A C 0.5282(3) 0.5536(3) 0.4309(2) 0.0417(6) Uani 1 1 d . . . . .
C00B C 0.3249(3) 0.5351(3) 0.5656(2) 0.0466(7) Uani 1 1 d . . . . .
H00A H 0.219744 0.501970 0.553710 0.056 Uiso 1 1 calc R U . . .
H00B H 0.324602 0.590423 0.630765 0.056 Uiso 1 1 calc R U . . .
C00C C 0.7883(4) 0.5756(3) 0.5228(2) 0.0458(7) Uani 1 1 d . . . . .
H00C H 0.863942 0.629879 0.553486 0.055 Uiso 1 1 calc R U . . .
C00D C 0.6584(4) 0.6282(2) 0.4820(3) 0.0485(7) Uani 1 1 d . . . . .
H00D H 0.648361 0.717977 0.485625 0.058 Uiso 1 1 calc R U . . .
C00E C 0.4347(5) 0.3416(5) 0.7790(3) 0.0729(11) Uani 1 1 d . . . . .
H00E H 0.364581 0.411714 0.795946 0.109 Uiso 1 1 calc R U . . .
H00F H 0.522082 0.343525 0.829321 0.109 Uiso 1 1 calc R U . . .
H00G H 0.380183 0.260580 0.786654 0.109 Uiso 1 1 calc R U . . .
C00F C 0.5289(5) 0.5651(4) 0.3046(2) 0.0673(10) Uani 1 1 d . . . . .
H00H H 0.437202 0.523524 0.274935 0.101 Uiso 1 1 calc R U . . .
H00I H 0.621128 0.523885 0.275461 0.101 Uiso 1 1 calc R U . . .
H00J H 0.528738 0.655006 0.283933 0.101 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
O001 C004 1.214(3) . ?
O002 C00A 1.455(4) . ?
O002 C00B 1.438(3) . ?
O003 C008 1.210(3) . ?
C004 C007 1.519(4) . ?
C004 C00C 1.467(4) . ?
C005 H005 0.9800 . ?
C005 C006 1.496(3) . ?
C005 C007 1.531(3) . ?
C005 C00A 1.529(3) . ?
C006 C009 1.336(4) . ?
C006 C00B 1.472(4) . ?
C007 H007 0.9800 . ?
C007 C008 1.554(3) . ?
C008 C009 1.474(4) . ?
C009 C00E 1.500(4) . ?
C00A C00D 1.484(4) . ?
C00A C00F 1.525(3) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9300 . ?
C00C C00D 1.327(5) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9600 . ?
C00E H00F 0.9600 . ?
C00E H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00F H00I 0.9600 . ?
C00F H00J 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
C00B O002 C00A 110.7(2) . . ?
O001 C004 C007 120.5(2) . . ?
O001 C004 C00C 121.3(3) . . ?
C00C C004 C007 118.2(2) . . ?
C006 C005 H005 110.0 . . ?
C006 C005 C007 104.08(18) . . ?
C006 C005 C00A 100.89(18) . . ?
C007 C005 H005 110.0 . . ?
C00A C005 H005 110.0 . . ?
C00A C005 C007 121.0(2) . . ?
C009 C006 C005 114.0(2) . . ?
C009 C006 C00B 137.0(2) . . ?
C00B C006 C005 108.2(2) . . ?
C004 C007 C005 114.2(2) . . ?
C004 C007 H007 110.7 . . ?
C004 C007 C008 107.71(19) . . ?
C005 C007 H007 110.7 . . ?
C005 C007 C008 102.5(2) . . ?
C008 C007 H007 110.7 . . ?
O003 C008 C007 125.2(2) . . ?
O003 C008 C009 126.8(2) . . ?
C009 C008 C007 107.9(2) . . ?
C006 C009 C008 108.2(2) . . ?
C006 C009 C00E 129.8(3) . . ?
C008 C009 C00E 121.9(3) . . ?
O002 C00A C005 103.4(2) . . ?
O002 C00A C00D 109.4(2) . . ?
O002 C00A C00F 107.1(2) . . ?
C00D C00A C005 111.2(2) . . ?
C00D C00A C00F 111.7(3) . . ?
C00F C00A C005 113.5(2) . . ?
O002 C00B C006 104.8(2) . . ?
O002 C00B H00A 110.8 . . ?
O002 C00B H00B 110.8 . . ?
C006 C00B H00A 110.8 . . ?
C006 C00B H00B 110.8 . . ?
H00A C00B H00B 108.9 . . ?
C004 C00C H00C 118.6 . . ?
C00D C00C C004 122.7(3) . . ?
C00D C00C H00C 118.6 . . ?
C00A C00D H00D 117.8 . . ?
C00C C00D C00A 124.4(2) . . ?
C00C C00D H00D 117.8 . . ?
C009 C00E H00E 109.5 . . ?
C009 C00E H00F 109.5 . . ?
C009 C00E H00G 109.5 . . ?
H00E C00E H00F 109.5 . . ?
H00E C00E H00G 109.5 . . ?
H00F C00E H00G 109.5 . . ?
C00A C00F H00H 109.5 . . ?
C00A C00F H00I 109.5 . . ?
C00A C00F H00J 109.5 . . ?
H00H C00F H00I 109.5 . . ?
H00H C00F H00J 109.5 . . ?
H00I C00F H00J 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
O001 C004 C007 C005 -170.2(2) . . . . ?
O001 C004 C007 C008 76.6(3) . . . . ?
O001 C004 C00C C00D 162.3(3) . . . . ?
O002 C00A C00D C00C 137.4(3) . . . . ?
O003 C008 C009 C006 -175.4(3) . . . . ?
O003 C008 C009 C00E 7.2(5) . . . . ?
C004 C007 C008 O003 -72.0(3) . . . . ?
C004 C007 C008 C009 104.7(2) . . . . ?
C004 C00C C00D C00A 0.2(4) . . . . ?
C005 C006 C009 C008 4.2(3) . . . . ?
C005 C006 C009 C00E -178.7(3) . . . . ?
C005 C006 C00B O002 -16.8(3) . . . . ?
C005 C007 C008 O003 167.3(3) . . . . ?
C005 C007 C008 C009 -16.0(2) . . . . ?
C005 C00A C00D C00C 23.7(4) . . . . ?
C006 C005 C007 C004 -98.7(2) . . . . ?
C006 C005 C007 C008 17.5(2) . . . . ?
C006 C005 C00A O002 -33.4(2) . . . . ?
C006 C005 C00A C00D 83.9(3) . . . . ?
C006 C005 C00A C00F -149.1(3) . . . . ?
C007 C004 C00C C00D -19.3(4) . . . . ?
C007 C005 C006 C009 -14.5(3) . . . . ?
C007 C005 C006 C00B 157.4(2) . . . . ?
C007 C005 C00A O002 -147.3(2) . . . . ?
C007 C005 C00A C00D -29.9(3) . . . . ?
C007 C005 C00A C00F 97.0(3) . . . . ?
C007 C008 C009 C006 7.9(3) . . . . ?
C007 C008 C009 C00E -169.5(3) . . . . ?
C009 C006 C00B O002 152.3(3) . . . . ?
C00A O002 C00B C006 -5.9(3) . . . . ?
C00A C005 C006 C009 -140.6(2) . . . . ?
C00A C005 C006 C00B 31.3(3) . . . . ?
C00A C005 C007 C004 13.5(3) . . . . ?
C00A C005 C007 C008 129.7(2) . . . . ?
C00B O002 C00A C005 25.3(3) . . . . ?
C00B O002 C00A C00D -93.3(3) . . . . ?
C00B O002 C00A C00F 145.5(3) . . . . ?
C00B C006 C009 C008 -164.5(3) . . . . ?
C00B C006 C009 C00E 12.7(6) . . . . ?
C00C C004 C007 C005 11.3(3) . . . . ?
C00C C004 C007 C008 -101.8(3) . . . . ?
C00F C00A C00D C00C -104.2(3) . . . . ?

_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 2.618
_oxdiff_exptl_absorpt_empirical_full_min 0.268
