# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_220708ky_auto
_database_code_depnum_ccdc_archive 'CCDC 2189245'
loop_
_audit_author_name
_audit_author_address
'Yousuke Yamaoka'
;Kyoto University
Japan
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_chemical_name_systematic        
(S)-3-[(R)-Bromo(4-methylphenyl)methyl]isobenzofuran-1(3H)-one
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_h-m   'P 43'
_symmetry_int_tables_number      78
_chemical_absolute_configuration ad
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/hexane'
_chemical_melting_point          434
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_diffrn_ambient_temperature      93
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   8.67730(10)
_cell_length_b                   8.67730(10)
_cell_length_c                   17.8920(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1347.19(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.8160
_cell_measurement_theta_min      5.0670
_shelx_estimated_absorpt_T_max   0.684
_shelx_estimated_absorpt_T_min   0.493
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9588
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.221
_diffrn_reflns_theta_min         5.097
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00  30.00   92
  2  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00   0.00   92
  3  ω   -136.00  43.00   0.50    0.50    --  -46.70  40.00 120.00  358
  4  ω   -136.00  43.00   0.50    0.50    --  -46.70  41.00 169.92  358
  5  ω   -146.00  -9.00   0.50    0.50    --  -97.40  45.00 174.81  274
  6  ω    -42.00  -8.00   0.50    0.50    --  -97.40  26.00 178.02   68
  7  ω    -35.00 -10.00   0.50    0.50    --  -97.40  32.00 179.74   50
  8  ω    -33.00  -8.00   0.50    0.50    --  -97.40  43.00 178.72   50
  9  ω   -141.00 -37.00   0.50    0.50    --  -97.40  59.00 118.47  208
 10  ω    -84.00 -58.00   0.50    0.50    --  -97.40  32.00 179.74   52
 11  ω    -35.00  -9.00   0.50    0.50    --  -97.40  44.00 165.51   52
 12  ω   -147.00 -39.00   0.50    0.50    --  -97.40  60.00  91.30  216
 13  ω   -122.00 -18.00   0.50    0.50    --  -97.40  40.00 150.00  208
 14  ω   -143.00 -26.00   0.50    0.50    --  -97.40  49.00 164.50  234
 15  ω    -38.00 -10.00   0.50    0.50    --  -97.40  44.00 170.60   56
 16  ω    -34.00  -9.00   0.50    0.50    --  -97.40  45.00 161.26   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1510848000
_diffrn_orient_matrix_UB_12      -0.0556810000
_diffrn_orient_matrix_UB_13      -0.0363554000
_diffrn_orient_matrix_UB_21      -0.0471921000
_diffrn_orient_matrix_UB_22      0.1683645000
_diffrn_orient_matrix_UB_23      -0.0141293000
_diffrn_orient_matrix_UB_31      0.0806815000
_diffrn_orient_matrix_UB_32      -0.0046845000
_diffrn_orient_matrix_UB_33      -0.0767750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                2554
_reflns_number_total             2584
_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       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.101
_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)+(0.1340P)²+1.7227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1657
_refine_special_details          ?
_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
Br01 Br 1.00832(12) 0.03561(8) 0.54639(6) 0.0229(3) Uani 1 1 d . . . . .
O002 O 0.6443(7) 0.0140(7) 0.5285(3) 0.0198(13) Uani 1 1 d . . . . .
O003 O 0.4008(8) 0.0093(8) 0.5710(3) 0.0247(14) Uani 1 1 d . . . . .
C004 C 0.7234(10) 0.4469(10) 0.6465(4) 0.0211(17) Uani 1 1 d . . . . .
H004 H 0.668290 0.441558 0.692323 0.025 Uiso 1 1 calc R U . . .
C005 C 0.4924(10) 0.0527(10) 0.5245(4) 0.0205(17) Uani 1 1 d . . . . .
C006 C 0.3368(11) 0.2226(11) 0.4313(5) 0.0246(18) Uani 1 1 d . . . . .
H006 H 0.239653 0.205787 0.454323 0.030 Uiso 1 1 calc R U . . .
C007 C 0.4696(10) 0.1526(10) 0.4582(4) 0.0204(16) Uani 1 1 d . . . . .
C008 C 0.8318(9) 0.3172(9) 0.5391(5) 0.0188(15) Uani 1 1 d . . . . .
C009 C 0.8650(10) 0.1779(10) 0.4930(4) 0.0190(16) Uani 1 1 d . . . . .
H009 H 0.920079 0.214284 0.447181 0.023 Uiso 1 1 calc R U . . .
C00A C 0.7740(11) 0.5900(11) 0.6209(5) 0.0233(17) Uani 1 1 d . . . . .
C00B C 0.6110(11) 0.1732(9) 0.4249(4) 0.0197(16) Uani 1 1 d . . . . .
C00C C 0.7511(10) 0.3121(10) 0.6070(4) 0.0210(16) Uani 1 1 d . . . . .
H00C H 0.715440 0.216246 0.625902 0.025 Uiso 1 1 calc R U . . .
C00D C 0.7289(10) 0.0811(10) 0.4666(4) 0.0203(17) Uani 1 1 d . . . . .
H00D H 0.767671 -0.003459 0.433589 0.024 Uiso 1 1 calc R U . . .
C00E C 0.7452(13) 0.7359(12) 0.6641(5) 0.030(2) Uani 1 1 d . . . . .
H00A H 0.640765 0.733726 0.685004 0.045 Uiso 1 1 calc R U . . .
H00B H 0.755602 0.824821 0.630721 0.045 Uiso 1 1 calc R U . . .
H00E H 0.820301 0.744287 0.704817 0.045 Uiso 1 1 calc R U . . .
C00F C 0.6278(11) 0.2691(11) 0.3633(5) 0.0231(17) Uani 1 1 d . . . . .
H00F H 0.725392 0.284520 0.340489 0.028 Uiso 1 1 calc R U . . .
C00G C 0.4970(11) 0.3413(11) 0.3365(5) 0.0255(18) Uani 1 1 d . . . . .
H00G H 0.505918 0.408384 0.294795 0.031 Uiso 1 1 calc R U . . .
C00H C 0.3516(12) 0.3187(11) 0.3690(5) 0.0276(19) Uani 1 1 d . . . . .
H00H H 0.263532 0.368413 0.348656 0.033 Uiso 1 1 calc R U . . .
C00I C 0.8535(11) 0.5949(10) 0.5525(5) 0.0259(17) Uani 1 1 d . . . . .
H00I H 0.888085 0.690855 0.533200 0.031 Uiso 1 1 calc R U . . .
C00J C 0.8818(11) 0.4593(11) 0.5126(5) 0.0241(18) Uani 1 1 d . . . . .
H00J H 0.936167 0.464268 0.466624 0.029 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
Br01 C009 1.996(8) . ?
O002 C005 1.362(10) . ?
O002 C00D 1.451(10) . ?
O003 C005 1.210(11) . ?
C004 C00A 1.394(13) . ?
C004 C00C 1.388(12) . ?
C005 C007 1.484(11) . ?
C006 C007 1.388(13) . ?
C006 C00H 1.398(12) . ?
C007 C00B 1.375(13) . ?
C008 C009 1.492(11) . ?
C008 C00C 1.402(11) . ?
C008 C00J 1.390(12) . ?
C009 C00D 1.525(12) . ?
C00A C00E 1.505(13) . ?
C00A C00I 1.406(13) . ?
C00B C00D 1.498(12) . ?
C00B C00F 1.388(12) . ?
C00F C00G 1.382(13) . ?
C00G C00H 1.403(13) . ?
C00I C00J 1.397(13) . ?

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
C005 O002 C00D 110.5(6) . . ?
C00C C004 C00A 121.9(8) . . ?
O002 C005 C007 108.4(7) . . ?
O003 C005 O002 121.5(8) . . ?
O003 C005 C007 130.1(8) . . ?
C007 C006 C00H 117.4(9) . . ?
C006 C007 C005 130.1(8) . . ?
C00B C007 C005 107.6(8) . . ?
C00B C007 C006 122.3(8) . . ?
C00C C008 C009 123.3(7) . . ?
C00J C008 C009 118.0(8) . . ?
C00J C008 C00C 118.6(8) . . ?
C008 C009 Br01 110.9(5) . . ?
C008 C009 C00D 117.9(7) . . ?
C00D C009 Br01 106.8(5) . . ?
C004 C00A C00E 121.8(8) . . ?
C004 C00A C00I 117.9(8) . . ?
C00I C00A C00E 120.3(8) . . ?
C007 C00B C00D 108.9(7) . . ?
C007 C00B C00F 121.0(8) . . ?
C00F C00B C00D 130.1(8) . . ?
C004 C00C C008 120.1(8) . . ?
O002 C00D C009 112.1(6) . . ?
O002 C00D C00B 104.4(7) . . ?
C00B C00D C009 112.9(7) . . ?
C00G C00F C00B 117.4(8) . . ?
C00F C00G C00H 122.1(8) . . ?
C006 C00H C00G 119.7(9) . . ?
C00J C00I C00A 120.3(8) . . ?
C008 C00J C00I 121.2(8) . . ?

