# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_pengty_0601
_database_code_depnum_ccdc_archive 'CCDC 2034163'
loop_
_audit_author_name
_audit_author_address
'Wang Hongyu'
;State key laboratory of applied organic chemistry
China
;
_audit_update_record             
;
2020-09-26 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_chemical_absolute_configuration ad
_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 0.0181 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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.20676(18)
_cell_length_b                   11.3756(2)
_cell_length_c                   12.0915(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1128.82(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3513
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      69.6420
_cell_measurement_theta_min      9.0910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01533
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7411
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.839
_diffrn_reflns_theta_min         5.339
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   9.00   1.00    1.00    --    0.00  57.00 -30.00   29
  2  ω     41.00  66.00   1.00    1.00    --    0.00  57.00 -30.00   25
  3  ω     34.00 116.00   1.00    1.00    --   54.00  57.00 -90.00   82
  4  ω     68.00 109.00   1.00    1.00    --   54.00  57.00 -30.00   41
  5  ω     91.00 156.00   1.00    1.00    --  108.00  63.00 -30.00   65
  6  ω    113.00 178.00   1.00    1.00    --  108.00 111.00  60.00   65
  7  ω     93.00 160.00   1.00    1.00    --  108.00  63.00   0.00   67
  8  ω     91.00 178.00   1.00    1.00    --  108.00  50.00 -90.00   87
  9  ω     97.00 123.00   1.00    1.00    --  108.00 -50.00-120.00   26
 10  ω     88.00 115.00   1.00    1.00    --  108.00-111.00-120.00   27
 11  ω     48.00 111.00   1.00    1.00    --   54.00-125.00-150.00   63
 12  ω     46.00 115.00   1.00    1.00    --  108.00 -77.00   0.00   69
 13  ω     83.00 116.00   1.00    1.00    --  108.00-111.00 120.00   33
 14  ω     76.00 145.00   1.00    1.00    --  108.00 -91.00 150.00   69
 15  ω     91.00 176.00   1.00    1.00    --  108.00  35.00 112.00   85
 16  ω     88.00 171.00   1.00    1.00    --  108.00  50.00 -60.00   83
 17  ω     49.00 126.00   1.00    1.00    --  108.00 -50.00 120.00   77
 18  ω     41.00  73.00   1.00    1.00    --  108.00 -91.00 150.00   32
 19  ω     36.00  64.00   1.00    1.00    --  108.00 -94.00 121.00   28
 20  ω     23.00  61.00   1.00    1.00    --   54.00-125.00 120.00   38
 21  ω     39.00 109.00   1.00    1.00    --  108.00-111.00   0.00   70
 22  ω     26.00  96.00   1.00    1.00    --   54.00 -19.00  90.00   70
 23  ω     21.00  74.00   1.00    1.00    --   54.00 -57.00 -60.00   53
 24  ω     10.00  55.00   1.00    1.00    --   54.00 -38.00-120.00   45
 25  ω      6.00  55.00   1.00    1.00    --    0.00  57.00-150.00   49
 26  ω     -9.00  16.00   1.00    1.00    --    0.00 -57.00  60.00   25
 27  ω    -16.00  64.00   1.00    1.00    --   54.00 -77.00 120.00   80
 28  ω    -69.00 -25.00   1.00    1.00    --    0.00 -57.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0109723000
_diffrn_orient_matrix_UB_12      -0.1253768000
_diffrn_orient_matrix_UB_13      0.0476798000
_diffrn_orient_matrix_UB_21      -0.1818179000
_diffrn_orient_matrix_UB_22      0.0052166000
_diffrn_orient_matrix_UB_23      0.0314217000
_diffrn_orient_matrix_UB_31      -0.0456358000
_diffrn_orient_matrix_UB_32      -0.0510299000
_diffrn_orient_matrix_UB_33      -0.1138111000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1994
_reflns_number_total             2108
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (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 (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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.108
_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)+(0.0664P)²+0.0349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1045
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O2 O 0.06213(19) 0.59428(13) 0.61670(12) 0.0540(4) Uani 1 1 d . . . . .
O3 O 0.27427(18) 0.67531(13) 0.45294(15) 0.0605(4) Uani 1 1 d . . . . .
O1 O -0.1488(3) 0.31273(19) 0.5136(2) 0.1062(9) Uani 1 1 d . . . . .
C2 C -0.0479(3) 0.45906(19) 0.39306(18) 0.0524(5) Uani 1 1 d . . . . .
C3 C -0.1770(3) 0.4450(2) 0.3198(3) 0.0751(8) Uani 1 1 d . . . . .
H3 H -0.255450 0.387838 0.333421 0.090 Uiso 1 1 calc R U . . .
C6 C 0.0554(3) 0.6154(2) 0.28060(19) 0.0644(6) Uani 1 1 d . . . . .
H6 H 0.132643 0.673408 0.266607 0.077 Uiso 1 1 calc R U . . .
C7 C 0.0709(2) 0.54415(17) 0.37375(15) 0.0462(4) Uani 1 1 d . . . . .
C5 C -0.0744(4) 0.6004(3) 0.2087(2) 0.0821(9) Uani 1 1 d . . . . .
H5 H -0.083870 0.648761 0.147019 0.099 Uiso 1 1 calc R U . . .
C10 C 0.1009(3) 0.39585(18) 0.56871(19) 0.0589(6) Uani 1 1 d . . . . .
H10A H 0.182659 0.338269 0.548206 0.071 Uiso 1 1 calc R U . . .
H10B H 0.066136 0.378417 0.643611 0.071 Uiso 1 1 calc R U . . .
C12 C 0.1283(3) 0.7101(2) 0.6228(2) 0.0670(6) Uani 1 1 d . . . . .
H12A H 0.226984 0.709269 0.667004 0.080 Uiso 1 1 calc R U . . .
H12B H 0.050636 0.762239 0.658210 0.080 Uiso 1 1 calc R U . . .
C9 C 0.1771(2) 0.51628(17) 0.56672(16) 0.0479(4) Uani 1 1 d . . . . .
H9 H 0.277069 0.515305 0.611009 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1659(3) 0.7539(2) 0.5097(2) 0.0657(6) Uani 1 1 d . . . . .
H11A H 0.065493 0.761546 0.467964 0.079 Uiso 1 1 calc R U . . .
H11B H 0.215625 0.831103 0.514755 0.079 Uiso 1 1 calc R U . . .
C4 C -0.1896(4) 0.5147(3) 0.2275(3) 0.0865(9) Uani 1 1 d . . . . .
H4 H -0.275293 0.504205 0.178180 0.104 Uiso 1 1 calc R U . . .
C8 C 0.2177(2) 0.55622(16) 0.44928(17) 0.0457(4) Uani 1 1 d . . . . .
C13 C 0.3615(3) 0.4865(2) 0.4032(2) 0.0626(6) Uani 1 1 d . . . . .
H13A H 0.391079 0.517197 0.331984 0.094 Uiso 1 1 calc R U . . .
H13B H 0.331335 0.405310 0.395897 0.094 Uiso 1 1 calc R U . . .
H13C H 0.452578 0.493093 0.452618 0.094 Uiso 1 1 calc R U . . .
C1 C -0.0410(3) 0.38368(17) 0.4934(2) 0.0611(6) Uani 1 1 d . . . . .


_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 C12 1.428(3) . ?
O2 C9 1.429(2) . ?
O3 C11 1.436(3) . ?
O3 C8 1.433(2) . ?
O1 C1 1.222(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.394(3) . ?
C2 C1 1.487(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C5 1.386(4) . ?
C7 C8 1.518(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.506(3) . ?
C10 C1 1.485(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.488(4) . ?
C9 H9 0.9800 . ?
C9 C8 1.528(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4 0.9300 . ?
C8 C13 1.528(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C12 O2 C9 110.12(17) . . ?
C8 O3 C11 113.75(15) . . ?
C3 C2 C7 120.4(2) . . ?
C3 C2 C1 118.9(2) . . ?
C7 C2 C1 120.69(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C2 C7 C8 121.16(17) . . ?
C6 C7 C2 118.4(2) . . ?
C6 C7 C8 120.40(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
H10A C10 H10B 107.7 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C1 C10 H10A 108.8 . . ?
C1 C10 H10B 108.8 . . ?
C1 C10 C9 113.62(17) . . ?
O2 C12 H12A 109.7 . . ?
O2 C12 H12B 109.7 . . ?
O2 C12 C11 109.90(18) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
O2 C9 C10 106.50(16) . . ?
O2 C9 H9 109.2 . . ?
O2 C9 C8 110.63(15) . . ?
C10 C9 H9 109.2 . . ?
C10 C9 C8 112.08(17) . . ?
C8 C9 H9 109.2 . . ?
O3 C11 C12 111.0(2) . . ?
O3 C11 H11A 109.4 . . ?
O3 C11 H11B 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C8 C7 111.19(16) . . ?
O3 C8 C9 108.85(17) . . ?
O3 C8 C13 104.58(16) . . ?
C7 C8 C9 111.06(15) . . ?
C7 C8 C13 110.28(17) . . ?
C9 C8 C13 110.69(17) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C1 C2 121.1(3) . . ?
O1 C1 C10 120.4(2) . . ?
C10 C1 C2 118.47(18) . . ?

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
O2 C12 C11 O3 -56.4(3) . . . . ?
O2 C9 C8 O3 55.6(2) . . . . ?
O2 C9 C8 C7 -67.1(2) . . . . ?
O2 C9 C8 C13 170.04(17) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C7 C8 O3 -150.04(17) . . . . ?
C2 C7 C8 C9 -28.7(2) . . . . ?
C2 C7 C8 C13 94.4(2) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C3 C2 C7 C8 -176.54(19) . . . . ?
C3 C2 C1 O1 -2.1(3) . . . . ?
C3 C2 C1 C10 177.5(2) . . . . ?
C6 C7 C8 O3 32.5(2) . . . . ?
C6 C7 C8 C9 153.85(17) . . . . ?
C6 C7 C8 C13 -83.1(2) . . . . ?
C6 C5 C4 C3 1.2(4) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C7 C2 C1 O1 176.5(2) . . . . ?
C7 C2 C1 C10 -3.9(3) . . . . ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 C6 C7 C8 176.8(2) . . . . ?
C10 C9 C8 O3 174.33(15) . . . . ?
C10 C9 C8 C7 51.6(2) . . . . ?
C10 C9 C8 C13 -71.3(2) . . . . ?
C12 O2 C9 C10 177.31(17) . . . . ?
C12 O2 C9 C8 -60.7(2) . . . . ?
C9 O2 C12 C11 60.5(2) . . . . ?
C9 C10 C1 O1 -152.6(2) . . . . ?
C9 C10 C1 C2 27.8(3) . . . . ?
C11 O3 C8 C7 69.9(2) . . . . ?
C11 O3 C8 C9 -52.7(2) . . . . ?
C11 O3 C8 C13 -171.1(2) . . . . ?
C8 O3 C11 C12 54.2(3) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C7 C6 -177.63(18) . . . . ?
C1 C2 C7 C8 4.8(3) . . . . ?
C1 C10 C9 O2 69.0(2) . . . . ?
C1 C10 C9 C8 -52.1(2) . . . . ?

_olex2_date_sample_data_collection 2020-06-01
_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 48.687
_oxdiff_exptl_absorpt_empirical_full_min 0.582
