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

data_3aa
_database_code_depnum_ccdc_archive 'CCDC 2350164'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2024-04-22 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
#mo_v607_GuillotICMMO_T100K



_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O4'
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.2670(4)
_cell_length_b                   24.5964(17)
_cell_length_c                   8.6870(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.236(2)
_cell_angle_gamma                90
_cell_volume                     1328.40(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.58


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8428
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_process_details   'Bruker APEX2'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43783
_diffrn_reflns_av_unetI/netI     0.1601
_diffrn_reflns_av_R_equivalents  0.1547
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.504
_diffrn_reflns_theta_max         32.640
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4855
_reflns_number_gt                3046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4855
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.88326(17) 0.44363(5) 0.67026(13) 0.0124(2) Uani 1 1 d . . . . .
C2 C 0.56043(17) 0.39876(5) 0.65803(12) 0.0113(2) Uani 1 1 d . . . . .
H2 H 0.437058 0.414623 0.705447 0.014 Uiso 1 1 calc R U . . .
C3 C 0.57686(16) 0.42685(5) 0.50493(12) 0.0109(2) Uani 1 1 d . . . . .
C4 C 0.76353(17) 0.45405(5) 0.51724(13) 0.0121(2) Uani 1 1 d . . . . .
H4 H 0.810641 0.476510 0.439184 0.014 Uiso 1 1 calc R U . . .
C5 C 0.41140(17) 0.42493(5) 0.36920(12) 0.0109(2) Uani 1 1 d . . . . .
C6 C 0.45317(18) 0.44800(5) 0.22828(13) 0.0140(2) Uani 1 1 d . . . . .
H6 H 0.589476 0.463948 0.220556 0.017 Uiso 1 1 calc R U . . .
C7 C 0.29668(19) 0.44767(6) 0.10017(13) 0.0182(3) Uani 1 1 d . . . . .
H7 H 0.325800 0.463737 0.005574 0.022 Uiso 1 1 calc R U . . .
C8 C 0.09682(19) 0.42385(5) 0.10971(14) 0.0181(3) Uani 1 1 d . . . . .
H8 H -0.009784 0.423445 0.021684 0.022 Uiso 1 1 calc R U . . .
C9 C 0.05457(18) 0.40084(5) 0.24788(14) 0.0161(3) Uani 1 1 d . . . . .
H9 H -0.081079 0.384327 0.254235 0.019 Uiso 1 1 calc R U . . .
C10 C 0.20940(17) 0.40167(5) 0.37786(13) 0.0131(2) Uani 1 1 d . . . . .
H10 H 0.177740 0.386386 0.472826 0.016 Uiso 1 1 calc R U . . .
C11 C 0.53859(17) 0.33708(5) 0.65423(12) 0.0114(2) Uani 1 1 d . . . . .
H11 H 0.416080 0.328421 0.572654 0.014 Uiso 1 1 calc R U . . .
C12 C 0.73219(17) 0.30758(5) 0.60956(13) 0.0132(2) Uani 1 1 d . . . . .
C13 C 0.56798(18) 0.25057(6) 0.76759(14) 0.0177(3) Uani 1 1 d . . . . .
H13A H 0.612699 0.230108 0.864420 0.021 Uiso 1 1 calc R U . . .
H13B H 0.451638 0.230206 0.704778 0.021 Uiso 1 1 calc R U . . .
C14 C 0.49160(17) 0.30766(5) 0.80441(13) 0.0129(2) Uani 1 1 d . . . . .
C15 C 0.25190(18) 0.30898(6) 0.82309(16) 0.0218(3) Uani 1 1 d . . . . .
H15A H 0.227919 0.289136 0.917214 0.033 Uiso 1 1 calc R U . . .
H15B H 0.169100 0.291878 0.732690 0.033 Uiso 1 1 calc R U . . .
H15C H 0.205292 0.346791 0.831334 0.033 Uiso 1 1 calc R U . . .
C16 C 0.62519(19) 0.32864(6) 0.95154(13) 0.0175(3) Uani 1 1 d . . . . .
H16A H 0.584539 0.366290 0.970501 0.026 Uiso 1 1 calc R U . . .
H16B H 0.778216 0.327145 0.938702 0.026 Uiso 1 1 calc R U . . .
H16C H 0.598569 0.305937 1.039858 0.026 Uiso 1 1 calc R U . . .
O1 O 1.06235(12) 0.45748(4) 0.72466(10) 0.0168(2) Uani 1 1 d . . . . .
O2 O 0.75949(12) 0.41262(4) 0.75388(9) 0.01291(18) Uani 1 1 d . . . . .
O3 O 0.85834(14) 0.32174(4) 0.52336(10) 0.0190(2) Uani 1 1 d . . . . .
O4 O 0.75046(13) 0.25846(4) 0.68040(10) 0.0180(2) 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
C1 O1 1.2106(13) . ?
C1 O2 1.3612(14) . ?
C1 C4 1.4644(14) . ?
C2 O2 1.4505(11) . ?
C2 C3 1.5137(16) . ?
C2 C11 1.5232(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.3402(16) . ?
C3 C5 1.4696(14) . ?
C4 H4 0.9500 . ?
C5 C10 1.3998(15) . ?
C5 C6 1.4035(16) . ?
C6 C7 1.3876(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.3947(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3825(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3932(14) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.5059(16) . ?
C11 C14 1.5521(16) . ?
C11 H11 1.0000 . ?
C12 O3 1.2067(14) . ?
C12 O4 1.3543(15) . ?
C13 O4 1.4619(15) . ?
C13 C14 1.5301(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.5268(16) . ?
C14 C15 1.5315(15) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 C1 O2 120.80(10) . . ?
O1 C1 C4 130.46(11) . . ?
O2 C1 C4 108.74(9) . . ?
O2 C2 C3 104.38(9) . . ?
O2 C2 C11 108.36(8) . . ?
C3 C2 C11 116.84(9) . . ?
O2 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C11 C2 H2 109.0 . . ?
C4 C3 C5 126.92(11) . . ?
C4 C3 C2 108.24(9) . . ?
C5 C3 C2 124.82(10) . . ?
C3 C4 C1 109.11(10) . . ?
C3 C4 H4 125.4 . . ?
C1 C4 H4 125.4 . . ?
C10 C5 C6 118.78(10) . . ?
C10 C5 C3 121.44(10) . . ?
C6 C5 C3 119.77(10) . . ?
C7 C6 C5 120.43(11) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.27(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.69(10) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.51(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.31(11) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C2 114.35(9) . . ?
C12 C11 C14 103.67(9) . . ?
C2 C11 C14 118.18(9) . . ?
C12 C11 H11 106.6 . . ?
C2 C11 H11 106.6 . . ?
C14 C11 H11 106.6 . . ?
O3 C12 O4 120.99(11) . . ?
O3 C12 C11 129.28(11) . . ?
O4 C12 C11 109.72(10) . . ?
O4 C13 C14 105.80(10) . . ?
O4 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O4 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C16 C14 C13 109.40(9) . . ?
C16 C14 C15 110.23(11) . . ?
C13 C14 C15 112.24(11) . . ?
C16 C14 C11 113.82(10) . . ?
C13 C14 C11 98.90(10) . . ?
C15 C14 C11 111.81(9) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O2 C2 109.39(8) . . ?
C12 O4 C13 109.08(9) . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062



