# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_yu167
_database_code_depnum_ccdc_archive 'CCDC 2204195'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_audit_creation_date             2022-08-29
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_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 .
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5249(6)
_cell_length_b                   7.7533(9)
_cell_length_c                   11.3333(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.142(3)
_cell_angle_gamma                90
_cell_volume                     558.33(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7129
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      3.21
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1530 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.9159.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17343
_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         26.743
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2063
_reflns_number_total             2381
_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       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.041
_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)+(0.0667P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1387
_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. Restrained distances
 C5-C3 \\sim C5-C3'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3')
4. Rigid body (RIGU) restrains
 O1', C1', C2', C3', C4', O2'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Same fragment restrains
{O1, O2, C1, C2, C3, C4} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1', O2', C1', C2', C3', C4'}
6. Others
 Sof(O1')=Sof(O2')=Sof(C1')=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(C3')=Sof(H3')=
 Sof(C4')=Sof(H4'A)=Sof(H4'B)=Sof(H5B)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(H5A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C3(H3), C3'(H3')
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C2'(H2'A,H2'B), C4'(H4'A,H4'B)
7.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C5(H5B), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
7.d 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 1.2995(5) 0.5602(6) 0.9958(3) 0.0631(13) Uani 0.735(7) 1 d D . P A 1
O2 O 0.9818(6) 0.6665(5) 0.9869(3) 0.0562(11) Uani 0.735(7) 1 d D . P A 1
C1 C 1.1187(11) 0.5644(15) 0.9444(10) 0.051(2) Uani 0.735(7) 1 d D . P A 1
C2 C 1.0045(10) 0.4801(10) 0.8286(6) 0.0503(16) Uani 0.735(7) 1 d D . P A 1
H2A H 1.045004 0.357202 0.826824 0.060 Uiso 0.735(7) 1 calc R U P A 1
H2B H 1.036510 0.539268 0.757488 0.060 Uiso 0.735(7) 1 calc R U P A 1
C3 C 0.7708(11) 0.4974(15) 0.8288(8) 0.0513(16) Uani 0.735(7) 1 d D . P A 1
H3 H 0.727666 0.397949 0.873846 0.062 Uiso 0.735(7) 1 calc R U P A 1
C4 C 0.7759(9) 0.6610(9) 0.9039(6) 0.0524(14) Uani 0.735(7) 1 d D . P A 1
H4A H 0.755045 0.763888 0.850777 0.063 Uiso 0.735(7) 1 calc R U P A 1
H4B H 0.663301 0.658164 0.949477 0.063 Uiso 0.735(7) 1 calc R U P A 1
O1' O 1.1925(19) 0.6554(16) 1.0580(8) 0.070(4) Uani 0.265(7) 1 d D . P A 2
O2' O 1.1726(16) 0.4722(14) 0.9069(9) 0.052(3) Uani 0.265(7) 1 d D . P A 2
C1' C 1.090(4) 0.596(5) 0.965(3) 0.051(5) Uani 0.265(7) 1 d D . P A 2
C2' C 0.860(3) 0.620(2) 0.9109(18) 0.058(4) Uani 0.265(7) 1 d D . P A 2
H2'A H 0.833564 0.733390 0.870151 0.070 Uiso 0.265(7) 1 calc R U P A 2
H2'B H 0.777760 0.613002 0.974216 0.070 Uiso 0.265(7) 1 calc R U P A 2
C3' C 0.799(3) 0.474(5) 0.820(2) 0.0513(16) Uani 0.265(7) 1 d D . P A 2
H3' H 0.745501 0.378505 0.863628 0.062 Uiso 0.265(7) 1 calc R U P A 2
C4' C 1.013(3) 0.417(3) 0.8048(18) 0.049(4) Uani 0.265(7) 1 d D . P A 2
H4'A H 1.016091 0.289243 0.798304 0.059 Uiso 0.265(7) 1 calc R U P A 2
H4'B H 1.040901 0.466036 0.729443 0.059 Uiso 0.265(7) 1 calc R U P A 2
O3 O -0.1169(4) 0.4560(4) 0.2150(2) 0.0617(8) Uani 1 1 d . . . . .
C5 C 0.6306(5) 0.5064(5) 0.7065(3) 0.0466(8) Uani 1 1 d D . . . .
H5A H 0.664852 0.588484 0.651819 0.056 Uiso 0.735(7) 1 calc R U P A 1
H5B H 0.647173 0.604930 0.659754 0.056 Uiso 0.265(7) 1 calc R U P A 2
C6 C 0.4615(6) 0.4101(5) 0.6666(3) 0.0506(8) Uani 1 1 d . . . . .
H6 H 0.432743 0.325022 0.720990 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3134(5) 0.4195(5) 0.5480(3) 0.0465(8) Uani 1 1 d . . . . .
C8 C 0.1212(6) 0.3335(5) 0.5304(4) 0.0555(9) Uani 1 1 d . . . . .
H8 H 0.091331 0.266699 0.594727 0.067 Uiso 1 1 calc R U . . .
C9 C -0.0268(6) 0.3424(5) 0.4222(4) 0.0550(9) Uani 1 1 d . . . . .
H9 H -0.158085 0.284973 0.413277 0.066 Uiso 1 1 calc R U . . .
C10 C 0.0169(5) 0.4352(5) 0.3274(3) 0.0492(8) Uani 1 1 d . . . . .
C11 C 0.2087(5) 0.5181(4) 0.3408(3) 0.0472(8) Uani 1 1 d . . . . .
H11 H 0.239630 0.580044 0.274620 0.057 Uiso 1 1 calc R U . . .
C12 C 0.3538(5) 0.5112(4) 0.4488(3) 0.0476(8) Uani 1 1 d . . . . .
H12 H 0.484323 0.569532 0.456878 0.057 Uiso 1 1 calc R U . . .
C13 C -0.3243(6) 0.3936(6) 0.1998(4) 0.0626(11) Uani 1 1 d . . . . .
H13A H -0.390394 0.446572 0.260328 0.094 Uiso 1 1 calc R U . . .
H13B H -0.321142 0.268027 0.210130 0.094 Uiso 1 1 calc R U . . .
H13C H -0.405332 0.422666 0.118367 0.094 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 C1 1.191(7) . ?
O2 C1 1.361(10) . ?
O2 C4 1.455(6) . ?
C1 C2 1.504(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(8) . ?
C3 H3 1.0000 . ?
C3 C4 1.524(10) . ?
C3 C5 1.478(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O1' C1' 1.199(18) . ?
O2' C1' 1.35(2) . ?
O2' C4' 1.436(18) . ?
C1' C2' 1.50(2) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C2' C3' 1.53(2) . ?
C3' H3' 1.0000 . ?
C3' C4' 1.51(2) . ?
C3' C5 1.51(2) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
O3 C10 1.380(4) . ?
O3 C13 1.410(4) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C5 C6 1.324(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.468(5) . ?
C7 C8 1.394(5) . ?
C7 C12 1.405(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(5) . ?
C10 C11 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(5) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C1 O2 C4 109.7(5) . . ?
O1 C1 O2 120.0(7) . . ?
O1 C1 C2 130.8(8) . . ?
O2 C1 C2 109.1(5) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.9(6) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 C2 100.3(6) . . ?
C4 C3 H3 109.2 . . ?
C5 C3 C2 114.0(7) . . ?
C5 C3 H3 109.2 . . ?
C5 C3 C4 114.5(7) . . ?
O2 C4 C3 106.6(5) . . ?
O2 C4 H4A 110.4 . . ?
O2 C4 H4B 110.4 . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C1' O2' C4' 108.3(13) . . ?
O1' C1' O2' 120(2) . . ?
O1' C1' C2' 128(2) . . ?
O2' C1' C2' 111.0(14) . . ?
C1' C2' H2'A 110.6 . . ?
C1' C2' H2'B 110.6 . . ?
C1' C2' C3' 105.6(14) . . ?
H2'A C2' H2'B 108.7 . . ?
C3' C2' H2'A 110.6 . . ?
C3' C2' H2'B 110.6 . . ?
C2' C3' H3' 106.0 . . ?
C4' C3' C2' 101.0(14) . . ?
C4' C3' H3' 106.0 . . ?
C5 C3' C2' 119(2) . . ?
C5 C3' H3' 106.0 . . ?
C5 C3' C4' 118(2) . . ?
O2' C4' C3' 109.9(13) . . ?
O2' C4' H4'A 109.7 . . ?
O2' C4' H4'B 109.7 . . ?
C3' C4' H4'A 109.7 . . ?
C3' C4' H4'B 109.7 . . ?
H4'A C4' H4'B 108.2 . . ?
C10 O3 C13 117.4(3) . . ?
C3 C5 H5A 117.1 . . ?
C3' C5 H5B 117.0 . . ?
C6 C5 C3 125.7(6) . . ?
C6 C5 C3' 125.9(15) . . ?
C6 C5 H5A 117.1 . . ?
C6 C5 H5B 117.0 . . ?
C5 C6 H6 116.2 . . ?
C5 C6 C7 127.5(3) . . ?
C7 C6 H6 116.2 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 C12 117.0(3) . . ?
C12 C7 C6 123.6(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
O3 C10 C11 114.4(3) . . ?
C9 C10 O3 125.6(3) . . ?
C9 C10 C11 120.0(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C1 C2 C3 166.0(13) . . . . ?
O2 C1 C2 C3 -17.8(12) . . . . ?
C1 O2 C4 C3 20.4(9) . . . . ?
C1 C2 C3 C4 28.1(10) . . . . ?
C1 C2 C3 C5 150.9(9) . . . . ?
C2 C3 C4 O2 -29.5(8) . . . . ?
C2 C3 C5 C6 128.9(7) . . . . ?
C3 C5 C6 C7 177.3(5) . . . . ?
C4 O2 C1 O1 175.2(10) . . . . ?
C4 O2 C1 C2 -1.4(11) . . . . ?
C4 C3 C5 C6 -116.5(8) . . . . ?
O1' C1' C2' C3' -162(4) . . . . ?
O2' C1' C2' C3' 8(4) . . . . ?
C1' O2' C4' C3' -17(3) . . . . ?
C1' C2' C3' C4' -17(3) . . . . ?
C1' C2' C3' C5 -147(3) . . . . ?
C2' C3' C4' O2' 20(3) . . . . ?
C2' C3' C5 C6 -128(2) . . . . ?
C3' C5 C6 C7 -168.7(14) . . . . ?
C4' O2' C1' O1' 176(3) . . . . ?
C4' O2' C1' C2' 5(4) . . . . ?
C4' C3' C5 C6 110(2) . . . . ?
O3 C10 C11 C12 178.4(3) . . . . ?
C5 C3 C4 O2 -152.0(6) . . . . ?
C5 C3' C4' O2' 152(2) . . . . ?
C5 C6 C7 C8 -166.7(4) . . . . ?
C5 C6 C7 C12 13.5(5) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C6 C7 C12 C11 -178.9(3) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C8 C7 C12 C11 1.3(5) . . . . ?
C8 C9 C10 O3 -179.5(3) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C7 0.5(5) . . . . ?
C12 C7 C8 C9 -2.3(5) . . . . ?
C13 O3 C10 C9 7.5(5) . . . . ?
C13 O3 C10 C11 -172.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
####################################################################### 
# 
# 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_yu228_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2252736'
loop_
_audit_author_name
_audit_author_address
'Jake Bailey'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 F O2'
_chemical_formula_sum            'C12 H11 F O2'
_chemical_formula_weight         206.21
_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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1406(5)
_cell_length_b                   5.8085(3)
_cell_length_c                   19.8674(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.646(2)
_cell_angle_gamma                90
_cell_volume                     938.42(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.342
_cell_measurement_theta_min      3.164
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1376 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.8250.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14833
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1641
_reflns_number_total             1919
_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       'APEX4 v2022.1-1 (Bruker, 2022)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.4832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0897
_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:
 C7(H7), C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_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
F1 F 0.22345(10) 0.78950(15) 0.85008(4) 0.0268(2) Uani 1 1 d . . . . .
O1 O 0.44083(11) 0.66555(16) 0.57859(5) 0.0210(2) Uani 1 1 d . . . . .
O2 O 0.24338(11) 0.55389(15) 0.50448(4) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.16625(16) 0.5426(2) 0.68349(6) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.111799 0.577274 0.641390 0.021 Uiso 1 1 calc R U . . .
C2 C 0.15243(16) 0.6947(2) 0.73696(7) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.089875 0.832216 0.731965 0.023 Uiso 1 1 calc R U . . .
C3 C 0.23258(16) 0.6393(2) 0.79757(6) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.32115(16) 0.4398(2) 0.80717(6) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.372540 0.404758 0.849848 0.024 Uiso 1 1 calc R U . . .
C5 C 0.33389(16) 0.2901(2) 0.75297(6) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.395068 0.151716 0.758815 0.022 Uiso 1 1 calc R U . . .
C6 C 0.25824(16) 0.3399(2) 0.69008(6) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.27670(16) 0.1784(2) 0.63160(6) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.325235 0.030557 0.648987 0.020 Uiso 1 1 calc R U . . .
C8 C 0.37239(16) 0.2562(2) 0.56828(6) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.483977 0.186601 0.564617 0.020 Uiso 1 1 calc R U . . .
C9 C 0.36167(15) 0.5104(2) 0.55331(6) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.18486(16) 0.3406(2) 0.47266(6) 0.0183(3) Uani 1 1 d . . . . .
H10A H 0.235767 0.317854 0.428844 0.022 Uiso 1 1 calc R U . . .
H10B H 0.063850 0.343905 0.464998 0.022 Uiso 1 1 calc R U . . .
C11 C 0.23559(16) 0.1498(2) 0.52147(6) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.266356 0.001820 0.499633 0.021 Uiso 1 1 calc R U . . .
C12 C 0.12681(16) 0.1221(2) 0.58311(6) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.083659 -0.035828 0.588525 0.023 Uiso 1 1 calc R U . . .
H12B H 0.037175 0.236976 0.584485 0.023 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
F1 C3 1.3644(15) . ?
O1 C9 1.2041(16) . ?
O2 C9 1.3586(15) . ?
O2 C10 1.4609(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3902(19) . ?
C1 C6 1.3982(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3808(19) . ?
C3 C4 1.374(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3916(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3974(18) . ?
C6 C7 1.5064(17) . ?
C7 H7 1.0000 . ?
C7 C8 1.5762(17) . ?
C7 C12 1.5540(18) . ?
C8 H8 1.0000 . ?
C8 C9 1.5079(18) . ?
C8 C11 1.5463(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5171(18) . ?
C11 H11 1.0000 . ?
C11 C12 1.5524(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C9 O2 C10 110.95(9) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.70(12) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.82(13) . . ?
C3 C2 H2 121.1 . . ?
F1 C3 C2 118.53(12) . . ?
F1 C3 C4 118.68(12) . . ?
C4 C3 C2 122.79(12) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.49(12) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.14(13) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.62(11) . . ?
C5 C6 C1 118.03(12) . . ?
C5 C6 C7 120.35(12) . . ?
C6 C7 H7 108.7 . . ?
C6 C7 C8 120.50(11) . . ?
C6 C7 C12 120.38(11) . . ?
C8 C7 H7 108.7 . . ?
C12 C7 H7 108.7 . . ?
C12 C7 C8 88.19(9) . . ?
C7 C8 H8 115.2 . . ?
C9 C8 C7 114.34(10) . . ?
C9 C8 H8 115.2 . . ?
C9 C8 C11 103.84(10) . . ?
C11 C8 C7 89.80(10) . . ?
C11 C8 H8 115.2 . . ?
O1 C9 O2 120.45(12) . . ?
O1 C9 C8 128.73(12) . . ?
O2 C9 C8 110.82(11) . . ?
O2 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
O2 C10 C11 105.61(10) . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C8 C11 H11 114.6 . . ?
C8 C11 C12 89.33(9) . . ?
C10 C11 C8 105.06(10) . . ?
C10 C11 H11 114.6 . . ?
C10 C11 C12 115.57(11) . . ?
C12 C11 H11 114.6 . . ?
C7 C12 H12A 113.6 . . ?
C7 C12 H12B 113.6 . . ?
C11 C12 C7 90.40(10) . . ?
C11 C12 H12A 113.6 . . ?
C11 C12 H12B 113.6 . . ?
H12A C12 H12B 110.8 . . ?

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
F1 C3 C4 C5 -178.27(12) . . . . ?
O2 C10 C11 C8 -18.79(13) . . . . ?
O2 C10 C11 C12 77.83(13) . . . . ?
C1 C2 C3 F1 178.46(12) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C6 C7 C8 65.86(17) . . . . ?
C1 C6 C7 C12 -41.77(17) . . . . ?
C2 C1 C6 C5 1.51(19) . . . . ?
C2 C1 C6 C7 -178.39(12) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -0.22(19) . . . . ?
C4 C5 C6 C1 -1.31(19) . . . . ?
C4 C5 C6 C7 178.59(12) . . . . ?
C5 C6 C7 C8 -114.04(14) . . . . ?
C5 C6 C7 C12 138.34(13) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C7 C8 C9 -30.87(17) . . . . ?
C6 C7 C8 C11 -136.00(12) . . . . ?
C6 C7 C12 C11 136.06(12) . . . . ?
C7 C8 C9 O1 81.81(17) . . . . ?
C7 C8 C9 O2 -97.87(12) . . . . ?
C7 C8 C11 C10 127.71(10) . . . . ?
C7 C8 C11 C12 11.36(10) . . . . ?
C8 C7 C12 C11 11.31(10) . . . . ?
C8 C11 C12 C7 -11.52(10) . . . . ?
C9 O2 C10 C11 18.81(13) . . . . ?
C9 C8 C11 C10 12.65(13) . . . . ?
C9 C8 C11 C12 -103.70(10) . . . . ?
C10 O2 C9 O1 169.53(11) . . . . ?
C10 O2 C9 C8 -10.76(13) . . . . ?
C10 C11 C12 C7 -117.93(12) . . . . ?
C11 C8 C9 O1 177.98(12) . . . . ?
C11 C8 C9 O2 -1.70(13) . . . . ?
C12 C7 C8 C9 93.78(12) . . . . ?
C12 C7 C8 C11 -11.35(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
