# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_dm_sl_xx_autored
_audit_block_doi                 10.5517/ccdc.csd.cc2myfz0
_database_code_depnum_ccdc_archive 'CCDC 2441373'
loop_
_audit_author_name
_audit_author_address
'Sudip Laru'
;STUDENT 
India
;
_audit_update_record             
;
2025-04-06 deposited with the CCDC.	2025-06-20 downloaded from the CCDC.
;
_audit_creation_date             2025-04-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 B2 Cl O4'
_chemical_formula_sum            'C27 H27 B2 Cl O4'
_chemical_formula_weight         472.55
_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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.4401(4)
_cell_length_b                   10.9000(3)
_cell_length_c                   17.4319(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.099(3)
_cell_angle_gamma                90
_cell_volume                     2534.15(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6204
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      21.8720
_cell_measurement_theta_min      2.0330
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.097
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51748
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.040
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -74.56 134.44   1.00    3.00  77.88 -12.98  31.50    --   209
  2  ω   -108.63  15.37   1.00    3.00    --  -12.98 -59.25  20.08  124
  3  φ   -119.92  64.08   1.00    3.00  16.12 -12.98 -59.25    --   184
  4  φ     46.57 230.57   1.00    3.00   9.42 -12.98 -31.50    --   184
  5  ω   -108.63  15.37   1.00    3.00    --  -12.98 -59.25-135.92  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0446600000
_diffrn_orient_matrix_UB_12      0.0321790000
_diffrn_orient_matrix_UB_13      -0.0133407000
_diffrn_orient_matrix_UB_21      -0.0140330000
_diffrn_orient_matrix_UB_22      -0.0475870000
_diffrn_orient_matrix_UB_23      -0.0269305000
_diffrn_orient_matrix_UB_31      -0.0252624000
_diffrn_orient_matrix_UB_32      -0.0305202000
_diffrn_orient_matrix_UB_33      0.0279008000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3200
_reflns_number_total             4452
_reflns_odcompleteness_completeness 90.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.26
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0773
_refine_ls_restrained_S_all      1.083
_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)+(0.1075P)²+3.1682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2318
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00E(H00E), C00F(H00F), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00V(H00B,H00C,H00D), C00W(H00G,H00H,H00I), C00X(H00J,H00L,H00V), C00Y(H00W,
 H00X,H00Y)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
Cl01 Cl 0.24553(7) 0.46449(11) 0.19074(7) 0.0648(4) Uani 1 1 d . . . . .
O002 O 0.76143(17) 0.3407(2) 0.25348(14) 0.0434(6) Uani 1 1 d . . . . .
O003 O 0.75509(19) 0.6721(2) 0.42448(13) 0.0454(6) Uani 1 1 d . . . . .
O004 O 0.62270(18) 0.3327(2) 0.15295(14) 0.0475(6) Uani 1 1 d . . . . .
H004 H 0.657325 0.275204 0.138104 0.071 Uiso 1 1 calc GR . . . .
O005 O 0.6242(2) 0.5590(2) 0.45415(15) 0.0536(7) Uani 1 1 d . . . . .
C006 C 0.6278(2) 0.4770(3) 0.27273(18) 0.0348(7) Uani 1 1 d . . . . .
C007 C 0.5318(2) 0.5437(3) 0.26142(17) 0.0344(7) Uani 1 1 d . . . . .
C008 C 0.4450(2) 0.4827(3) 0.23135(18) 0.0380(8) Uani 1 1 d . . . . .
H008 H 0.448078 0.400089 0.214425 0.046 Uiso 1 1 calc R . . . .
C009 C 0.6993(2) 0.4919(3) 0.33330(18) 0.0351(7) Uani 1 1 d . . . . .
C00A C 0.5250(3) 0.6668(3) 0.2815(2) 0.0413(8) Uani 1 1 d . . . . .
H00A H 0.584228 0.710802 0.299964 0.050 Uiso 1 1 calc R . . . .
C00B C 0.7887(2) 0.4079(3) 0.32509(19) 0.0400(8) Uani 1 1 d . . . . .
C00C C 0.3543(2) 0.5432(3) 0.22630(18) 0.0399(8) Uani 1 1 d . . . . .
C00D C 0.8077(3) 0.3125(3) 0.3896(2) 0.0438(8) Uani 1 1 d . . . . .
C00E C 0.4341(3) 0.7255(3) 0.2750(2) 0.0493(9) Uani 1 1 d . . . . .
H00E H 0.431046 0.809565 0.288950 0.059 Uiso 1 1 calc R . . . .
C00F C 0.3468(3) 0.6635(3) 0.2483(2) 0.0480(9) Uani 1 1 d . . . . .
H00F H 0.283395 0.702988 0.245354 0.058 Uiso 1 1 calc R . . . .
B B 0.6931(3) 0.5763(3) 0.4047(2) 0.0350(8) Uani 1 1 d . . . . .
C00H C 0.8818(3) 0.4842(3) 0.3171(2) 0.0490(9) Uani 1 1 d . . . . .
B00I B 0.6673(3) 0.3771(4) 0.2198(2) 0.0390(9) Uani 1 1 d . . . . .
C00J C 0.7257(3) 0.7277(4) 0.4947(2) 0.0570(11) Uani 1 1 d . . . . .
C00K C 0.8908(3) 0.2393(4) 0.3958(3) 0.0620(11) Uani 1 1 d . . . . .
H00K H 0.938471 0.249780 0.360303 0.074 Uiso 1 1 calc R . . . .
C00L C 0.6440(4) 0.6442(4) 0.5179(2) 0.0685(13) Uani 1 1 d . . . . .
C00M C 0.9449(3) 0.5210(4) 0.3834(3) 0.0667(12) Uani 1 1 d . . . . .
H00M H 0.929733 0.496849 0.432989 0.080 Uiso 1 1 calc R . . . .
C00N C 0.9071(4) 0.1504(4) 0.4523(3) 0.0726(13) Uani 1 1 d . . . . .
H00N H 0.964908 0.099709 0.454251 0.087 Uiso 1 1 calc R . . . .
C00O C 0.7386(3) 0.2911(4) 0.4419(3) 0.0684(12) Uani 1 1 d . . . . .
H00O H 0.678514 0.337753 0.438136 0.082 Uiso 1 1 calc R . . . .
C00P C 0.8429(4) 0.1343(4) 0.5045(3) 0.0741(13) Uani 1 1 d . . . . .
H00P H 0.857007 0.075886 0.544818 0.089 Uiso 1 1 calc R . . . .
C00Q C 0.9030(4) 0.5228(5) 0.2470(3) 0.0768(14) Uani 1 1 d . . . . .
H00Q H 0.859502 0.501971 0.201702 0.092 Uiso 1 1 calc R . . . .
C00R C 0.7568(4) 0.2026(5) 0.4992(3) 0.0846(16) Uani 1 1 d . . . . .
H00R H 0.709649 0.189435 0.534695 0.102 Uiso 1 1 calc R . . . .
C00S C 1.0284(4) 0.5918(5) 0.3773(4) 0.0867(17) Uani 1 1 d . . . . .
H00S H 1.070007 0.618085 0.422307 0.104 Uiso 1 1 calc R . . . .
C00T C 1.0507(4) 0.6236(5) 0.3052(5) 0.101(2) Uani 1 1 d . . . . .
H00T H 1.110627 0.667652 0.300597 0.122 Uiso 1 1 calc R . . . .
C00U C 0.9896(5) 0.5940(6) 0.2410(4) 0.102(2) Uani 1 1 d . . . . .
H00U H 1.004508 0.620727 0.191821 0.123 Uiso 1 1 calc R . . . .
C00V C 0.6783(7) 0.8536(6) 0.4649(5) 0.145(4) Uani 1 1 d . . . . .
H00B H 0.719136 0.889978 0.427973 0.217 Uiso 1 1 calc GR . . . .
H00C H 0.676262 0.909389 0.508769 0.217 Uiso 1 1 calc GR . . . .
H00D H 0.610079 0.839742 0.439474 0.217 Uiso 1 1 calc GR . . . .
C00W C 0.8137(5) 0.7556(11) 0.5457(4) 0.179(5) Uani 1 1 d . . . . .
H00G H 0.845454 0.679237 0.565759 0.268 Uiso 1 1 calc GR . . . .
H00H H 0.795810 0.805309 0.588797 0.268 Uiso 1 1 calc GR . . . .
H00I H 0.860537 0.801504 0.517699 0.268 Uiso 1 1 calc GR . . . .
C00X C 0.6886(12) 0.5628(9) 0.5849(4) 0.243(8) Uani 1 1 d . . . . .
H00J H 0.664188 0.478580 0.576260 0.364 Uiso 1 1 calc GR . . . .
H00L H 0.668302 0.593867 0.633411 0.364 Uiso 1 1 calc GR . . . .
H00V H 0.761918 0.563668 0.588097 0.364 Uiso 1 1 calc GR . . . .
C00Y C 0.5528(7) 0.6937(10) 0.5351(8) 0.244(8) Uani 1 1 d . . . . .
H00W H 0.527080 0.751804 0.494574 0.366 Uiso 1 1 calc GR . . . .
H00X H 0.563615 0.736267 0.584960 0.366 Uiso 1 1 calc GR . . . .
H00Y H 0.504081 0.627386 0.537837 0.366 Uiso 1 1 calc GR . . . .


_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
Cl01 C00C 1.742(3) . ?
O002 C00B 1.455(4) . ?
O002 B00I 1.385(5) . ?
O003 B 1.354(4) . ?
O003 C00J 1.463(4) . ?
O004 B00I 1.335(5) . ?
O005 B 1.354(4) . ?
O005 C00L 1.448(5) . ?
C006 C007 1.473(4) . ?
C006 C009 1.346(4) . ?
C006 B00I 1.562(5) . ?
C007 C008 1.388(5) . ?
C007 C00A 1.393(5) . ?
C008 C00C 1.379(5) . ?
C009 C00B 1.532(4) . ?
C009 B 1.558(5) . ?
C00A C00E 1.372(5) . ?
C00B C00D 1.530(5) . ?
C00B C00H 1.523(5) . ?
C00C C00F 1.373(5) . ?
C00D C00K 1.367(5) . ?
C00D C00O 1.398(6) . ?
C00E C00F 1.385(5) . ?
C00H C00M 1.404(6) . ?
C00H C00Q 1.356(6) . ?
C00J C00L 1.519(6) . ?
C00J C00V 1.573(8) . ?
C00J C00W 1.422(7) . ?
C00K C00N 1.380(6) . ?
C00L C00X 1.530(10) . ?
C00L C00Y 1.405(9) . ?
C00M C00S 1.377(7) . ?
C00N C00P 1.341(7) . ?
C00O C00R 1.389(6) . ?
C00P C00R 1.369(7) . ?
C00Q C00U 1.413(8) . ?
C00S C00T 1.372(9) . ?
C00T C00U 1.343(9) . ?

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
B00I O002 C00B 109.8(3) . . ?
B O003 C00J 108.1(3) . . ?
B O005 C00L 108.9(3) . . ?
C007 C006 B00I 128.4(3) . . ?
C009 C006 C007 125.0(3) . . ?
C009 C006 B00I 106.6(3) . . ?
C008 C007 C006 119.7(3) . . ?
C008 C007 C00A 118.6(3) . . ?
C00A C007 C006 121.7(3) . . ?
C00C C008 C007 119.3(3) . . ?
C006 C009 C00B 110.3(3) . . ?
C006 C009 B 126.5(3) . . ?
C00B C009 B 123.2(3) . . ?
C00E C00A C007 120.9(3) . . ?
O002 C00B C009 105.3(3) . . ?
O002 C00B C00D 106.8(3) . . ?
O002 C00B C00H 108.6(3) . . ?
C00D C00B C009 113.5(3) . . ?
C00H C00B C009 110.2(3) . . ?
C00H C00B C00D 112.0(3) . . ?
C008 C00C Cl01 118.9(3) . . ?
C00F C00C Cl01 118.8(3) . . ?
C00F C00C C008 122.3(3) . . ?
C00K C00D C00B 121.0(3) . . ?
C00K C00D C00O 117.0(4) . . ?
C00O C00D C00B 121.9(3) . . ?
C00A C00E C00F 120.7(3) . . ?
C00C C00F C00E 118.1(3) . . ?
O003 B O005 113.1(3) . . ?
O003 B C009 124.6(3) . . ?
O005 B C009 122.3(3) . . ?
C00M C00H C00B 120.0(4) . . ?
C00Q C00H C00B 121.2(4) . . ?
C00Q C00H C00M 118.7(4) . . ?
O002 B00I C006 108.0(3) . . ?
O004 B00I O002 123.7(3) . . ?
O004 B00I C006 128.3(3) . . ?
O003 C00J C00L 104.7(3) . . ?
O003 C00J C00V 103.0(4) . . ?
C00L C00J C00V 109.5(5) . . ?
C00W C00J O003 108.8(4) . . ?
C00W C00J C00L 122.3(5) . . ?
C00W C00J C00V 106.9(7) . . ?
C00D C00K C00N 121.5(4) . . ?
O005 C00L C00J 104.5(3) . . ?
O005 C00L C00X 103.4(5) . . ?
C00J C00L C00X 108.9(6) . . ?
C00Y C00L O005 109.1(5) . . ?
C00Y C00L C00J 120.3(6) . . ?
C00Y C00L C00X 109.2(9) . . ?
C00S C00M C00H 120.8(5) . . ?
C00P C00N C00K 121.2(4) . . ?
C00R C00O C00D 120.8(4) . . ?
C00N C00P C00R 119.5(4) . . ?
C00H C00Q C00U 120.2(5) . . ?
C00P C00R C00O 119.9(5) . . ?
C00T C00S C00M 119.0(6) . . ?
C00U C00T C00S 121.5(5) . . ?
C00T C00U C00Q 119.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.245
_oxdiff_exptl_absorpt_empirical_full_min 0.473
