# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_yy081
_database_code_depnum_ccdc_archive 'CCDC 2152111'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2023-01-01 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            TJ-PhBF
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         240.25
_chemical_absolute_configuration .

_chemical_melting_point          ?

_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                   8.3998(14)
_cell_length_b                   5.6694(9)
_cell_length_c                   12.814(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.089(6)
_cell_angle_gamma                90
_cell_volume                     586.32(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7901
_cell_measurement_theta_min      2.5236
_cell_measurement_theta_max      25.1218
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            24439
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2895
_reflns_number_gt                2369
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.996

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0957
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         2895
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.0335P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 840 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)

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'

_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6157(3) 0.6692(5) 0.85744(18) 0.0558(6) Uani d . . . 1 . .
C C2 0.7153(3) 0.4669(5) 0.86845(18) 0.0569(6) Uani d . . . 1 . .
C C3 0.7803(3) 0.3944(4) 0.7865(2) 0.0552(6) Uani d . . . 1 . .
H H3 0.84428 0.258524 0.792411 0.066 Uiso calc U . R 1 . .
C C4 0.7455(3) 0.5342(4) 0.69501(18) 0.0468(5) Uani d . . . 1 . .
C C5 0.6524(2) 0.7390(4) 0.68211(17) 0.0464(5) Uani d . . . 1 . .
C C6 0.5843(3) 0.8067(5) 0.7663(2) 0.0566(6) Uani d . . . 1 . .
H H6 0.519373 0.941665 0.760077 0.068 Uiso calc U . R 1 . .
C C7 0.6476(3) 0.8252(4) 0.57642(18) 0.0505(5) Uani d . . . 1 . .
H H7 0.594867 0.961686 0.544044 0.061 Uiso calc U . R 1 . .
C C8 0.7338(2) 0.6718(4) 0.53214(17) 0.0448(5) Uani d . . . 1 . .
C C9 0.7688(2) 0.6546(4) 0.42709(16) 0.0444(5) Uani d . . . 1 . .
C C10 0.7127(3) 0.8291(5) 0.3489(2) 0.0569(6) Uani d . . . 1 . .
H H10 0.655912 0.9588 0.364995 0.068 Uiso calc U . R 1 . .
C C11 0.7402(3) 0.8118(5) 0.2481(2) 0.0640(7) Uani d . . . 1 . .
H H11 0.701688 0.928927 0.196502 0.077 Uiso calc U . R 1 . .
C C12 0.8252(3) 0.6202(6) 0.2238(2) 0.0635(7) Uani d . . . 1 . .
H H12 0.843419 0.607312 0.155718 0.076 Uiso calc U . R 1 . .
C C13 0.8823(3) 0.4495(5) 0.3007(2) 0.0639(7) Uani d . . . 1 . .
H H13 0.94049 0.321388 0.284566 0.077 Uiso calc U . R 1 . .
C C14 0.8548(3) 0.4649(5) 0.40146(18) 0.0545(6) Uani d . . . 1 . .
H H14 0.894267 0.347171 0.452659 0.065 Uiso calc U . R 1 . .
C C15 0.8511(4) 0.1676(6) 0.9933(2) 0.0762(8) Uani d . . . 1 . .
H H15A 0.814822 0.040419 0.942833 0.114 Uiso calc U . R 1 . .
H H15B 0.858555 0.113594 1.0655 0.114 Uiso calc U . R 1 . .
H H15C 0.957977 0.221177 0.989856 0.114 Uiso calc U . R 1 . .
O O1 0.5492(2) 0.7310(4) 0.94039(14) 0.0795(7) Uani d . . . 1 . .
H H1 0.571954 0.629718 0.987883 0.119 Uiso calc U . R 1 . .
O O2 0.7372(2) 0.3540(5) 0.96655(15) 0.0841(7) Uani d . . . 1 . .
O O3 0.79614(18) 0.4900(3) 0.60373(11) 0.0486(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.368(4) ?
C1 O1 . 1.376(3) ?
C1 C2 . 1.403(4) ?
C2 C3 . 1.375(3) ?
C2 O2 . 1.377(3) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.93 ?
C4 O3 . 1.374(3) ?
C4 C5 . 1.384(3) ?
C5 C6 . 1.407(3) ?
C5 C7 . 1.430(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.353(3) ?
C7 H7 . 0.93 ?
C8 O3 . 1.382(3) ?
C8 C9 . 1.459(3) ?
C9 C14 . 1.385(3) ?
C9 C10 . 1.394(3) ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.369(4) ?
C12 H12 . 0.93 ?
C13 C14 . 1.376(3) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 O2 . 1.403(4) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
O1 H1 . 0.82 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 O1 . . 119.4(2) ?
C6 C1 C2 . . 121.4(2) ?
O1 C1 C2 . . 119.3(2) ?
C3 C2 O2 . . 125.3(2) ?
C3 C2 C1 . . 121.3(2) ?
O2 C2 C1 . . 113.4(2) ?
C2 C3 C4 . . 116.2(2) ?
C2 C3 H3 . . 121.9 ?
C4 C3 H3 . . 121.9 ?
O3 C4 C3 . . 125.2(2) ?
O3 C4 C5 . . 110.46(19) ?
C3 C4 C5 . . 124.4(2) ?
C4 C5 C6 . . 118.3(2) ?
C4 C5 C7 . . 105.47(19) ?
C6 C5 C7 . . 136.2(2) ?
C1 C6 C5 . . 118.4(2) ?
C1 C6 H6 . . 120.8 ?
C5 C6 H6 . . 120.8 ?
C8 C7 C5 . . 107.4(2) ?
C8 C7 H7 . . 126.3 ?
C5 C7 H7 . . 126.3 ?
C7 C8 O3 . . 110.45(19) ?
C7 C8 C9 . . 134.3(2) ?
O3 C8 C9 . . 115.24(18) ?
C14 C9 C10 . . 118.40(19) ?
C14 C9 C8 . . 121.51(19) ?
C10 C9 C8 . . 120.1(2) ?
C11 C10 C9 . . 120.8(2) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 119.9(2) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C13 C12 C11 . . 119.6(2) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.9(3) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C13 C14 C9 . . 120.4(2) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 O1 H1 . . 109.5 ?
C2 O2 C15 . . 118.9(2) ?
C4 O3 C8 . . 106.20(17) ?

