# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_BA
_database_code_depnum_ccdc_archive 'CCDC 2533705'
loop_
_audit_author_name
_audit_author_address
'Dr. P K Sudhadevi Antharjanam'
;SAIF, IIT Madras
India
;
_audit_update_record             
;
2026-02-27 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Benzoic acid'
_chemical_name_common            ?
_chemical_melting_point          394.25
_chemical_formula_moiety         'C7 H6 O2'
_chemical_formula_sum            'C7 H6 O2'
_chemical_formula_weight         122.12

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                   5.507(2)
_cell_length_b                   5.1404(16)
_cell_length_c                   21.964(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.038(12)
_cell_angle_gamma                90
_cell_volume                     617.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2029
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      25.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5362
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.    
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       'omega and phi scans'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5957
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.730
_diffrn_reflns_theta_max         25.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1175
_reflns_number_gt                863
_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       'APEX4 (Bruker, v2021.4-0)'
_computing_cell_refinement       'APEX4 V8.40B (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0526P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         1175
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.4582(4) 0.2710(4) 0.55758(10) 0.0421(5) Uani 1 1 d . . . . .
C2 C 0.4223(4) 0.4737(4) 0.60361(9) 0.0403(5) Uani 1 1 d . . . . .
C3 C 0.2131(4) 0.6266(5) 0.59740(12) 0.0548(7) Uani 1 1 d . . . . .
H3 H 0.093449 0.602195 0.564155 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1826(5) 0.8151(5) 0.64066(13) 0.0621(7) Uani 1 1 d . . . . .
H4 H 0.042569 0.917833 0.636364 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3581(5) 0.8516(5) 0.68996(12) 0.0608(7) Uani 1 1 d . . . . .
H5 H 0.336341 0.977788 0.719138 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5659(5) 0.7013(5) 0.69612(11) 0.0614(7) Uani 1 1 d . . . . .
H6 H 0.684992 0.726648 0.729437 0.074 Uiso 1 1 calc R U . . .
C7 C 0.5989(4) 0.5134(5) 0.65328(10) 0.0516(6) Uani 1 1 d . . . . .
H7 H 0.740327 0.412749 0.657684 0.062 Uiso 1 1 calc R U . . .
O1 O 0.2922(3) 0.2366(3) 0.51336(7) 0.0613(6) Uani 1 1 d . . . . .
H1 H 0.333070 0.120246 0.491189 0.092 Uiso 0.5 1 calc R U P . .
O2 O 0.6539(3) 0.1395(3) 0.56493(7) 0.0590(5) Uani 1 1 d . . . . .
H2 H 0.683314 0.083093 0.531686 0.088 Uiso 0.5 1 calc R U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0440(13) 0.0432(12) 0.0381(11) 0.0031(10) 0.0002(10) 0.0035(10)
C2 0.0411(12) 0.0414(12) 0.0384(11) 0.0026(9) 0.0051(9) -0.0006(9)
C3 0.0448(14) 0.0582(15) 0.0599(15) -0.0062(12) 0.0006(11) 0.0040(11)
C4 0.0533(15) 0.0561(15) 0.0790(18) -0.0078(14) 0.0163(13) 0.0090(12)
C5 0.0754(18) 0.0502(14) 0.0598(16) -0.0128(12) 0.0207(14) -0.0043(13)
C6 0.0733(18) 0.0595(16) 0.0485(14) -0.0094(12) -0.0038(12) 0.0000(13)
C7 0.0522(14) 0.0530(14) 0.0476(13) -0.0014(11) -0.0018(11) 0.0058(11)
O1 0.0624(11) 0.0636(11) 0.0529(10) -0.0133(8) -0.0135(8) 0.0161(9)
O2 0.0527(10) 0.0652(11) 0.0562(10) -0.0105(8) -0.0051(8) 0.0186(8)

_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 1.262(2) . ?
C1 O2 1.266(2) . ?
C1 C2 1.482(3) . ?
C2 C7 1.385(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?

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 123.3(2) . . ?
O1 C1 C2 118.63(19) . . ?
O2 C1 C2 118.10(19) . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C1 120.1(2) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C1 O1 H1 109.5 . . ?
C1 O2 H2 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 C7 178.9(2) . . . . ?
O2 C1 C2 C7 -0.6(3) . . . . ?
O1 C1 C2 C3 -1.5(3) . . . . ?
O2 C1 C2 C3 179.0(2) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C1 C2 C7 C6 -179.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.82 2.628(2) 166.2 3_656 yes
O2 H2 O1 0.82 1.93 2.628(2) 142.3 3_656 yes

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044

_shelx_res_file                  
;
TITL BA_a.res in P2(1)/n
    shelx.res
    created by SHELXL-2019/3 at 10:45:26 on 24-Oct-2025
CELL  0.71073   5.5072   5.1404  21.9644   90.000   97.038   90.000
ZERR     4.00   0.0022   0.0016   0.0079    0.000    0.012    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O
UNIT  28 24 8
MERG   2
EQIV $1 -x+1, -y, -z+1
HTAB O1 O2_$1
HTAB O2 O1_$1
FMAP   2
PLAN   20
SIZE     0.062   0.191   0.664
ACTA
BOND   $H
CONF
L.S.   4
TEMP    25.00
WGHT    0.052600    0.215300
FVAR       1.26026   0.50263   0.49737
C1    1    0.458152    0.270982    0.557580    11.00000    0.04395    0.04319 =
         0.03805    0.00308    0.00024    0.00353
C2    1    0.422286    0.473650    0.603612    11.00000    0.04111    0.04138 =
         0.03839    0.00264    0.00514   -0.00063
C3    1    0.213055    0.626576    0.597399    11.00000    0.04482    0.05815 =
         0.05988   -0.00622    0.00055    0.00402
AFIX  43
H3    2    0.093449    0.602195    0.564155    11.00000   -1.20000
AFIX   0
C4    1    0.182630    0.815103    0.640660    11.00000    0.05334    0.05612 =
         0.07904   -0.00784    0.01635    0.00900
AFIX  43
H4    2    0.042569    0.917833    0.636364    11.00000   -1.20000
AFIX   0
C5    1    0.358129    0.851558    0.689963    11.00000    0.07545    0.05016 =
         0.05983   -0.01278    0.02067   -0.00432
AFIX  43
H5    2    0.336341    0.977788    0.719138    11.00000   -1.20000
AFIX   0
C6    1    0.565928    0.701268    0.696120    11.00000    0.07332    0.05951 =
         0.04847   -0.00939   -0.00384   -0.00003
AFIX  43
H6    2    0.684992    0.726648    0.729437    11.00000   -1.20000
AFIX   0
C7    1    0.598930    0.513388    0.653276    11.00000    0.05216    0.05304 =
         0.04756   -0.00135   -0.00184    0.00576
AFIX  43
H7    2    0.740327    0.412749    0.657684    11.00000   -1.20000
AFIX   0
O1    3    0.292159    0.236597    0.513356    11.00000    0.06236    0.06363 =
         0.05286   -0.01327   -0.01346    0.01609
AFIX  83
H1    2    0.333070    0.120246    0.491189    10.50000   -1.50000
AFIX   0
O2    3    0.653918    0.139531    0.564927    11.00000    0.05270    0.06517 =
         0.05618   -0.01054   -0.00506    0.01857
AFIX  83
H2    2    0.683314    0.083093    0.531686    10.50000   -1.50000
AFIX   0
HKLF    4  1.0  1.00  0.00  0.00  0.00  1.00  0.00  0.00  0.00  1.00




REM  BA_a.res in P2(1)/n
REM wR2 = 0.1421, GooF = S = 1.119, Restrained GooF = 1.119 for all data
REM R1 = 0.0578 for 863 Fo > 4sig(Fo) and 0.0826 for all 1175 data
REM 84 parameters refined using 0 restraints

END

WGHT      0.0526      0.2153

REM Highest difference peak  0.132,  deepest hole -0.212,  1-sigma level  0.044
Q1    1   0.2622  0.8165  0.5439  11.00000  0.05    0.13
Q2    1   0.4283  0.1107  0.4569  11.00000  0.05    0.13
Q3    1   0.2614  1.1804  0.6748  11.00000  0.05    0.12
Q4    1   0.1924  0.9985  0.7278  11.00000  0.05    0.12
Q5    1   0.5647 -0.1170  0.6086  11.00000  0.05    0.12
Q6    1   0.7987  0.4741  0.6242  11.00000  0.05    0.12
Q7    1   0.2704  0.1130  0.4629  11.00000  0.05    0.12
Q8    1   0.1332  1.0644  0.6613  11.00000  0.05    0.12
Q9    1   0.4294  0.8161  0.5705  11.00000  0.05    0.11
Q10   1   0.3738  0.3383  0.4557  11.00000  0.05    0.11
Q11   1   0.2396  1.1601  0.7267  11.00000  0.05    0.11
Q12   1   0.1635  0.1625  0.5479  11.00000  0.05    0.11
Q13   1   0.4041  0.3124  0.6820  11.00000  0.05    0.11
Q14   1   0.3028  0.7851  0.6127  11.00000  0.05    0.11
Q15   1   0.0357  1.0215  0.6127  11.00000  0.05    0.11
Q16   1   0.6604  0.2781  0.6727  11.00000  0.05    0.11
Q17   1   0.7985  0.2306  0.5159  11.00000  0.05    0.11
Q18   1   0.2958  0.8516  0.7617  11.00000  0.05    0.11
Q19   1   0.2212  0.9049  0.5568  11.00000  0.05    0.10
Q20   1   0.3768  1.1984  0.7297  11.00000  0.05    0.10
;
_shelx_res_checksum              89815

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
