# Supplementary Information (SI) for ChemComm.
# 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).
# 
# 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_hbh_247_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2368719'
loop_
_audit_author_name
_audit_author_address
'Hemanga Bhattacharyya' 'Indian Institute of Technology, Guwahati'
_audit_update_record             
;
2024-07-08 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_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_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                   8.402(3)
_cell_length_b                   8.472(3)
_cell_length_c                   9.245(4)
_cell_angle_alpha                109.344(11)
_cell_angle_beta                 101.143(11)
_cell_angle_gamma                100.258(11)
_cell_volume                     588.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6544
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1435 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.9386.
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    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6996
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14188
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.001
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                1770
_reflns_number_total             2304
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.087
_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)+(0.0479P)²+0.1874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2967(2) 0.6537(3) 0.99819(18) 0.1035(6) Uani 1 1 d . . . . .
O2 O 0.21495(19) 0.2234(2) 0.11854(16) 0.0805(5) Uani 1 1 d . . . . .
O3 O 0.09385(18) 0.2747(3) 0.31600(18) 0.0919(6) Uani 1 1 d . . . . .
C1 C 0.4281(2) 0.3085(2) 0.5240(2) 0.0499(4) Uani 1 1 d . . . . .
C2 C 0.5806(2) 0.2883(2) 0.5974(2) 0.0555(5) Uani 1 1 d . . . . .
H2 H 0.622135 0.343136 0.707423 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6731(2) 0.1907(2) 0.5141(2) 0.0553(5) Uani 1 1 d . . . . .
C4 C 0.6099(2) 0.1032(2) 0.3492(2) 0.0541(5) Uani 1 1 d . . . . .
C5 C 0.4597(2) 0.1233(2) 0.2747(2) 0.0549(5) Uani 1 1 d . . . . .
H5 H 0.417844 0.066444 0.164809 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3685(2) 0.2251(2) 0.3575(2) 0.0505(4) Uani 1 1 d . . . . .
C7 C 0.3411(2) 0.4200(2) 0.6201(2) 0.0538(5) Uani 1 1 d . . . . .
H7 H 0.256699 0.452765 0.564841 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3701(2) 0.4788(3) 0.7769(2) 0.0616(5) Uani 1 1 d . . . . .
H8 H 0.450801 0.446311 0.836781 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2782(3) 0.5923(3) 0.8559(2) 0.0688(6) Uani 1 1 d . . . . .
H9 H 0.197656 0.620944 0.792015 0.083 Uiso 1 1 calc R U . . .
C10 C 0.8400(3) 0.1817(3) 0.6022(3) 0.0785(6) Uani 1 1 d . . . . .
H10A H 0.838416 0.062834 0.583121 0.118 Uiso 1 1 calc R U . . .
H10B H 0.860090 0.244827 0.714326 0.118 Uiso 1 1 calc R U . . .
H10C H 0.927856 0.231633 0.565344 0.118 Uiso 1 1 calc R U . . .
C11 C 0.7024(3) -0.0076(3) 0.2526(3) 0.0713(6) Uani 1 1 d . . . . .
H11A H 0.632588 -0.069740 0.145536 0.107 Uiso 1 1 calc R U . . .
H11B H 0.730034 -0.088582 0.299048 0.107 Uiso 1 1 calc R U . . .
H11C H 0.803783 0.064590 0.251524 0.107 Uiso 1 1 calc R U . . .
C12 C 0.2116(2) 0.2439(3) 0.2666(2) 0.0584(5) Uani 1 1 d . . . . .
C13 C 0.0695(3) 0.2418(4) 0.0192(3) 0.0970(9) Uani 1 1 d . . . . .
H13A H 0.081604 0.216039 -0.086766 0.145 Uiso 1 1 calc R U . . .
H13B H 0.060197 0.358542 0.062164 0.145 Uiso 1 1 calc R U . . .
H13C H -0.029728 0.163067 0.016090 0.145 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 C9 1.210(2) . ?
O2 C12 1.328(2) . ?
O2 C13 1.446(2) . ?
O3 C12 1.201(2) . ?
C1 C2 1.397(3) . ?
C1 C6 1.406(2) . ?
C1 C7 1.468(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 C4 1.398(3) . ?
C3 C10 1.508(3) . ?
C4 C5 1.384(3) . ?
C4 C11 1.502(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(2) . ?
C6 C12 1.485(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.323(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.439(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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 C13 116.51(17) . . ?
C2 C1 C6 117.31(16) . . ?
C2 C1 C7 119.80(16) . . ?
C6 C1 C7 122.82(16) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.17(18) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 119.11(17) . . ?
C2 C3 C10 119.65(18) . . ?
C4 C3 C10 121.23(18) . . ?
C3 C4 C11 121.69(17) . . ?
C5 C4 C3 118.32(17) . . ?
C5 C4 C11 119.97(17) . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.71(17) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C12 121.82(16) . . ?
C5 C6 C1 119.30(16) . . ?
C5 C6 C12 118.88(16) . . ?
C1 C7 H7 116.5 . . ?
C8 C7 C1 126.93(17) . . ?
C8 C7 H7 116.5 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.86(18) . . ?
C9 C8 H8 119.6 . . ?
O1 C9 C8 125.7(2) . . ?
O1 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C6 111.50(16) . . ?
O3 C12 O2 122.20(18) . . ?
O3 C12 C6 126.30(18) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 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
C1 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C3 C10 177.58(18) . . . . ?
C1 C6 C12 O2 152.61(18) . . . . ?
C1 C6 C12 O3 -26.9(3) . . . . ?
C1 C7 C8 C9 177.92(18) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C12 -177.36(17) . . . . ?
C2 C1 C7 C8 -15.6(3) . . . . ?
C2 C3 C4 C5 2.5(3) . . . . ?
C2 C3 C4 C11 -178.78(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C12 177.89(17) . . . . ?
C5 C6 C12 O2 -26.8(2) . . . . ?
C5 C6 C12 O3 153.7(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C7 C8 167.31(19) . . . . ?
C7 C1 C2 C3 -177.55(16) . . . . ?
C7 C1 C6 C5 179.15(16) . . . . ?
C7 C1 C6 C12 -0.2(3) . . . . ?
C7 C8 C9 O1 -179.3(2) . . . . ?
C10 C3 C4 C5 -177.06(18) . . . . ?
C10 C3 C4 C11 1.7(3) . . . . ?
C11 C4 C5 C6 -179.57(17) . . . . ?
C13 O2 C12 O3 0.6(3) . . . . ?
C13 O2 C12 C6 -179.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
