# 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_210604-bxh01-pwy
_database_code_depnum_ccdc_archive 'CCDC 2089005'
loop_
_audit_author_name
_audit_author_address
jiang
;northeast normal university
China
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2021-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6312(6)
_cell_length_b                   9.3841(11)
_cell_length_c                   11.0292(13)
_cell_angle_alpha                74.169(10)
_cell_angle_beta                 78.153(10)
_cell_angle_gamma                80.784(9)
_cell_volume                     545.41(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9310
_cell_measurement_theta_min      4.9220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3904
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.153
_diffrn_reflns_theta_min         3.720
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00   1.00   1.00    2.00    --   -9.92 -57.00-120.00   73
  2  ω    -18.00  79.00   1.00    2.00    --   11.09  77.00 150.00   97
  3  ω    -52.00  33.00   1.00    2.00    --   11.09 -77.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0440846000
_diffrn_orient_matrix_UB_12      0.0683312000
_diffrn_orient_matrix_UB_13      -0.0362741000
_diffrn_orient_matrix_UB_21      -0.1054350000
_diffrn_orient_matrix_UB_22      0.0397386000
_diffrn_orient_matrix_UB_23      0.0279269000
_diffrn_orient_matrix_UB_31      0.0609017000
_diffrn_orient_matrix_UB_32      0.0007424000
_diffrn_orient_matrix_UB_33      0.0500599000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1704
_reflns_number_total             2489
_reflns_odcompleteness_completeness 99.28
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.055
_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)+(0.0497P)²+0.0955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00A(H00A), C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F),
 C00H(H00I)
;
_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 1.0308(2) 0.23209(15) 0.95586(12) 0.0534(4) Uani 1 1 d . . . . .
O002 O 0.3323(3) 0.69399(14) 0.51947(14) 0.0584(4) Uani 1 1 d . . . . .
O003 O 0.2363(3) 0.90417(15) 0.59833(15) 0.0646(4) Uani 1 1 d . . . . .
C004 C 0.7613(3) 0.58503(19) 0.74908(17) 0.0400(4) Uani 1 1 d . . . . .
C005 C 0.4711(3) 0.68371(19) 0.61163(17) 0.0399(4) Uani 1 1 d . . . . .
C006 C 0.6407(3) 0.56971(19) 0.65484(17) 0.0413(4) Uani 1 1 d . . . . .
H006 H 0.674851 0.485192 0.622983 0.050 Uiso 1 1 calc R . . . .
C007 C 0.9506(3) 0.46230(19) 0.80285(18) 0.0432(4) Uani 1 1 d . . . . .
H007 H 1.066914 0.510722 0.828791 0.052 Uiso 1 1 calc R . . . .
C008 C 0.4131(3) 0.80839(19) 0.65848(19) 0.0454(4) Uani 1 1 d . . . . .
C009 C 1.0965(3) 0.3793(2) 0.70721(18) 0.0462(5) Uani 1 1 d . . . . .
H009 H 1.157634 0.433405 0.625664 0.055 Uiso 1 1 calc R . . . .
C00A C 0.8397(3) 0.3500(2) 0.92409(17) 0.0458(5) Uani 1 1 d . . . . .
H00A H 0.775100 0.397530 0.994796 0.055 Uiso 1 1 calc R . . . .
C00B C 0.6520(3) 0.2689(2) 0.89958(18) 0.0520(5) Uani 1 1 d . . . . .
H00B H 0.485517 0.299664 0.905228 0.062 Uiso 1 1 calc R . . . .
C00C C 0.7025(4) 0.7115(2) 0.79508(19) 0.0497(5) Uani 1 1 d . . . . .
H00C H 0.783869 0.720942 0.857367 0.060 Uiso 1 1 calc R . . . .
C00D C 1.1398(3) 0.2330(2) 0.73545(19) 0.0531(5) Uani 1 1 d . . . . .
H00D H 1.234079 0.184301 0.675914 0.064 Uiso 1 1 calc R . . . .
C00E C 1.0334(4) 0.1465(2) 0.8663(2) 0.0543(5) Uani 1 1 d . . . . .
H00E H 1.117459 0.045660 0.890310 0.065 Uiso 1 1 calc R . . . .
C00F C 0.5259(4) 0.8252(2) 0.7514(2) 0.0562(5) Uani 1 1 d . . . . .
H00F H 0.486240 0.909118 0.784090 0.067 Uiso 1 1 calc R . . . .
C00G C 0.1820(4) 0.8325(2) 0.5108(2) 0.0571(6) Uani 1 1 d . . . . .
H00G H 0.212757 0.894925 0.424446 0.069 Uiso 1 1 calc R . . . .
H00H H 0.011216 0.815586 0.531308 0.069 Uiso 1 1 calc R . . . .
C00H C 0.7647(4) 0.1474(2) 0.8689(2) 0.0602(6) Uani 1 1 d . . . . .
H00I H 0.691923 0.074470 0.851666 0.072 Uiso 1 1 calc R . . . .


_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 C00A 1.438(2) . ?
O001 C00E 1.430(2) . ?
O002 C005 1.379(2) . ?
O002 C00G 1.424(2) . ?
O003 C008 1.378(2) . ?
O003 C00G 1.421(2) . ?
C004 C006 1.402(2) . ?
C004 C007 1.519(2) . ?
C004 C00C 1.382(3) . ?
C005 C006 1.366(2) . ?
C005 C008 1.371(3) . ?
C007 C009 1.510(3) . ?
C007 C00A 1.545(3) . ?
C008 C00F 1.366(3) . ?
C009 C00D 1.316(3) . ?
C00A C00B 1.502(3) . ?
C00B C00H 1.307(3) . ?
C00C C00F 1.392(3) . ?
C00D C00E 1.504(3) . ?
C00E C00H 1.506(3) . ?

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
C00E O001 C00A 101.84(13) . . ?
C005 O002 C00G 105.88(14) . . ?
C008 O003 C00G 105.63(14) . . ?
C006 C004 C007 120.50(15) . . ?
C00C C004 C006 119.43(16) . . ?
C00C C004 C007 120.06(16) . . ?
C006 C005 O002 127.71(16) . . ?
C006 C005 C008 122.70(17) . . ?
C008 C005 O002 109.59(15) . . ?
C005 C006 C004 117.41(16) . . ?
C004 C007 C00A 112.59(14) . . ?
C009 C007 C004 114.10(15) . . ?
C009 C007 C00A 109.63(15) . . ?
C005 C008 O003 110.26(17) . . ?
C00F C008 O003 128.70(17) . . ?
C00F C008 C005 121.04(17) . . ?
C00D C009 C007 122.18(18) . . ?
O001 C00A C007 106.68(13) . . ?
O001 C00A C00B 102.32(15) . . ?
C00B C00A C007 112.80(15) . . ?
C00H C00B C00A 107.69(17) . . ?
C004 C00C C00F 122.26(18) . . ?
C009 C00D C00E 118.44(18) . . ?
O001 C00E C00D 108.37(16) . . ?
O001 C00E C00H 101.69(16) . . ?
C00D C00E C00H 107.51(16) . . ?
C008 C00F C00C 117.15(18) . . ?
O003 C00G O002 108.63(14) . . ?
C00B C00H C00E 107.85(19) . . ?

_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 1.564
_oxdiff_exptl_absorpt_empirical_full_min 0.482
