# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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. 
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#######################################################################

data_240106lu_lgpz028629_0m
_database_code_depnum_ccdc_archive 'CCDC 2327303'
loop_
_audit_author_name
_audit_author_address
'chenfei guan' 'Zhejiang University of Technology'
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-06-02 downloaded from the CCDC.
;
_audit_creation_date             2024-01-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 O'
_chemical_formula_sum            'C13 H12 O'
_chemical_formula_weight         184.23
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   5.9974(4)
_cell_length_b                   8.0073(6)
_cell_length_c                   41.526(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1994.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0784 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            16218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.625
_diffrn_reflns_theta_min         2.943
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1548
_reflns_number_total             2311
_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       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0697
_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)+(0.0738P)²+2.0114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1913
_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 Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C10(H10), C12(H12), C9(H9), C4(H4), C2(H2)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.4603(3) 0.8853(3) 0.46709(4) 0.0417(5) Uani 1 1 d . . . . .
C6 C 0.3933(4) 0.6730(3) 0.38814(6) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.2416(4) 0.5760(3) 0.36982(6) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.102122 0.545451 0.378922 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3432(4) 0.7255(3) 0.42000(6) 0.0304(5) Uani 1 1 d . . . . .
H7 H 0.206951 0.692809 0.429816 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7495(4) 0.8184(3) 0.39201(6) 0.0336(6) Uani 1 1 d . . . . .
H10 H 0.888590 0.849742 0.382878 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5985(4) 0.7193(3) 0.37373(6) 0.0297(5) Uani 1 1 d . . . . .
C8 C 0.4923(4) 0.8238(3) 0.43665(6) 0.0319(6) Uani 1 1 d . . . . .
C3 C 0.4998(4) 0.5682(3) 0.32470(6) 0.0350(6) Uani 1 1 d . . . . .
C12 C 0.6469(4) 0.6658(3) 0.34204(6) 0.0349(6) Uani 1 1 d . . . . .
H12 H 0.784061 0.697849 0.332419 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6975(4) 0.8691(3) 0.42239(6) 0.0349(6) Uani 1 1 d . . . . .
H9 H 0.800282 0.935675 0.434138 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2927(4) 0.5261(3) 0.33942(6) 0.0366(6) Uani 1 1 d . . . . .
H4 H 0.187629 0.461484 0.327686 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2605(5) 0.8386(4) 0.48317(7) 0.0468(7) Uani 1 1 d . . . . .
H13A H 0.131893 0.881966 0.471258 0.070 Uiso 1 1 calc R U . . .
H13B H 0.260761 0.885060 0.504999 0.070 Uiso 1 1 calc R U . . .
H13C H 0.251222 0.716546 0.484324 0.070 Uiso 1 1 calc R U . . .
C2 C 0.5581(5) 0.5097(4) 0.29227(7) 0.0496(8) Uani 1 1 d . . . . .
H2 H 0.680390 0.563095 0.282007 0.059 Uiso 1 1 calc R U . . .
C1 C 0.4575(6) 0.3908(5) 0.27607(8) 0.0669(10) Uani 1 1 d . . . . .
H1A H 0.334280 0.333640 0.285311 0.080 Uiso 1 1 calc R U . . .
H1B H 0.507916 0.361834 0.255116 0.080 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 C8 1.370(3) . ?
O1 C13 1.422(3) . ?
C6 C5 1.418(3) . ?
C6 C7 1.420(3) . ?
C6 C11 1.418(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.359(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.424(3) . ?
C10 C9 1.361(4) . ?
C11 C12 1.414(3) . ?
C8 C9 1.413(3) . ?
C3 C12 1.381(4) . ?
C3 C4 1.425(4) . ?
C3 C2 1.468(4) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C1 1.313(5) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?

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
C8 O1 C13 117.2(2) . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 C11 118.3(2) . . ?
C11 C6 C7 120.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(2) . . ?
C6 C11 C10 118.2(2) . . ?
C12 C11 C6 119.4(2) . . ?
C12 C11 C10 122.3(2) . . ?
O1 C8 C7 125.3(2) . . ?
O1 C8 C9 114.6(2) . . ?
C7 C8 C9 120.1(2) . . ?
C12 C3 C4 117.8(2) . . ?
C12 C3 C2 120.5(2) . . ?
C4 C3 C2 121.7(2) . . ?
C11 C12 H12 119.1 . . ?
C3 C12 C11 121.7(2) . . ?
C3 C12 H12 119.1 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C2 H2 116.8 . . ?
C1 C2 C3 126.3(3) . . ?
C1 C2 H2 116.8 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?

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 C8 C9 C10 -179.1(2) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C6 C7 C8 O1 178.3(2) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C6 C11 C12 C3 -0.5(4) . . . . ?
C5 C6 C7 C8 -178.1(2) . . . . ?
C5 C6 C11 C10 179.2(2) . . . . ?
C5 C6 C11 C12 -0.9(3) . . . . ?
C7 C6 C5 C4 -179.6(2) . . . . ?
C7 C6 C11 C10 -0.1(3) . . . . ?
C7 C6 C11 C12 179.8(2) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C10 C11 C12 C3 179.3(2) . . . . ?
C11 C6 C5 C4 1.1(3) . . . . ?
C11 C6 C7 C8 1.2(3) . . . . ?
C11 C10 C9 C8 0.3(4) . . . . ?
C12 C3 C4 C5 -1.6(4) . . . . ?
C12 C3 C2 C1 165.0(3) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C9 C10 C11 C12 179.5(2) . . . . ?
C4 C3 C12 C11 1.8(4) . . . . ?
C4 C3 C2 C1 -14.6(5) . . . . ?
C13 O1 C8 C7 2.4(4) . . . . ?
C13 O1 C8 C9 -177.7(2) . . . . ?
C2 C3 C12 C11 -177.8(2) . . . . ?
C2 C3 C4 C5 178.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
