# Supplementary Information (SI) for Chemical Science.
# 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. 
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data_mo_ac013061b_0m
_database_code_depnum_ccdc_archive 'CCDC 2337764'
loop_
_audit_author_name
_audit_author_address
'Jordi Benet'
;Institute of Chemical Research of Catalonia (ICIQ)
Spain
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2024-03-01
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 Br O'
_chemical_formula_sum            'C14 H17 Br O'
_chemical_formula_weight         281.18
_chemical_absolute_configuration ad
_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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2267(12)
_cell_length_b                   11.976(2)
_cell_length_c                   14.973(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1295.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6559
_cell_measurement_temperature    100.40
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    3.150
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0963 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.7968.
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14021
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.612
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      100.40
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean .
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   .
_diffrn_source_current           0.61
_diffrn_source_power             0.0305
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3516
_reflns_number_total             3880
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.2898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0653
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
Br1 Br 1.00595(4) 0.41162(2) 0.62376(2) 0.03022(8) Uani 1 1 d . . . . .
O1 O 0.9770(2) 0.40469(14) 0.27896(12) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.7881(4) 0.47895(18) 0.57987(17) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.690180 0.492003 0.620914 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7625(3) 0.50917(18) 0.49589(16) 0.0158(4) Uani 1 1 d . . . . .
C3 C 0.8936(3) 0.50310(17) 0.41634(15) 0.0151(4) Uani 1 1 d . . . . .
H3 H 1.024057 0.511650 0.437547 0.018 Uiso 1 1 calc R U . . .
C4 C 0.8384(3) 0.60670(17) 0.35993(15) 0.0165(4) Uani 1 1 d . . . . .
H4A H 0.922560 0.670185 0.371914 0.020 Uiso 1 1 calc R U . . .
H4B H 0.841627 0.589276 0.295312 0.020 Uiso 1 1 calc R U . . .
C5 C 0.6440(3) 0.63308(17) 0.38995(15) 0.0144(4) Uani 1 1 d . . . . .
C6 C 0.5171(4) 0.70692(17) 0.35276(15) 0.0185(4) Uani 1 1 d . . . . .
H6 H 0.546813 0.747010 0.299925 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3464(3) 0.72140(18) 0.39372(17) 0.0206(5) Uani 1 1 d . . . . .
H7 H 0.258394 0.771076 0.368362 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3032(3) 0.6636(2) 0.47178(17) 0.0212(5) Uani 1 1 d . . . . .
H8 H 0.186204 0.674490 0.499314 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4296(3) 0.5901(2) 0.50975(16) 0.0195(4) Uani 1 1 d . . . . .
H9 H 0.400059 0.550489 0.562817 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6009(3) 0.57595(18) 0.46818(16) 0.0158(4) Uani 1 1 d . . . . .
C11 C 0.8756(3) 0.39336(18) 0.36135(15) 0.0182(4) Uani 1 1 d . . . . .
C12 C 0.6785(3) 0.3731(2) 0.33003(18) 0.0224(5) Uani 1 1 d . . . . .
H12A H 0.636679 0.436825 0.294293 0.034 Uiso 1 1 calc R U . . .
H12B H 0.597370 0.364205 0.381982 0.034 Uiso 1 1 calc R U . . .
H12C H 0.674349 0.305150 0.293600 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9434(4) 0.29177(19) 0.41327(19) 0.0258(5) Uani 1 1 d . . . . .
H13A H 0.942768 0.226186 0.374133 0.039 Uiso 1 1 calc R U . . .
H13B H 0.861392 0.278468 0.464309 0.039 Uiso 1 1 calc R U . . .
H13C H 1.069478 0.305357 0.434740 0.039 Uiso 1 1 calc R U . . .
C14 C 1.1723(4) 0.4210(3) 0.2866(2) 0.0358(7) Uani 1 1 d . . . . .
H14A H 1.228866 0.417774 0.227218 0.054 Uiso 1 1 calc R U . . .
H14B H 1.225147 0.362198 0.324397 0.054 Uiso 1 1 calc R U . . .
H14C H 1.196815 0.494036 0.313606 0.054 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
Br1 C1 1.887(2) . ?
O1 C11 1.441(3) . ?
O1 C14 1.429(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.321(3) . ?
C2 C3 1.524(3) . ?
C2 C10 1.475(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.553(3) . ?
C3 C11 1.556(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.509(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.394(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(3) . ?
C11 C12 1.519(3) . ?
C11 C13 1.525(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C14 O1 C11 116.47(19) . . ?
Br1 C1 H1 117.8 . . ?
C2 C1 Br1 124.4(2) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 130.1(2) . . ?
C1 C2 C10 121.8(2) . . ?
C10 C2 C3 107.35(19) . . ?
C2 C3 H3 109.5 . . ?
C2 C3 C4 103.15(17) . . ?
C2 C3 C11 113.70(17) . . ?
C4 C3 H3 109.5 . . ?
C4 C3 C11 111.44(18) . . ?
C11 C3 H3 109.5 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 C3 104.15(17) . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C6 C5 C4 128.9(2) . . ?
C6 C5 C10 120.1(2) . . ?
C10 C5 C4 110.87(19) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 C2 109.03(19) . . ?
C5 C10 C9 120.9(2) . . ?
C9 C10 C2 130.0(2) . . ?
O1 C11 C3 109.33(17) . . ?
O1 C11 C12 103.14(19) . . ?
O1 C11 C13 110.39(19) . . ?
C12 C11 C3 112.12(18) . . ?
C12 C11 C13 109.32(19) . . ?
C13 C11 C3 112.17(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Br1 C1 C2 C3 -2.4(4) . . . . ?
Br1 C1 C2 C10 -170.96(16) . . . . ?
C1 C2 C3 C4 -147.1(2) . . . . ?
C1 C2 C3 C11 92.0(3) . . . . ?
C1 C2 C10 C5 155.7(2) . . . . ?
C1 C2 C10 C9 -21.6(4) . . . . ?
C2 C3 C4 C5 -21.7(2) . . . . ?
C2 C3 C11 O1 168.84(18) . . . . ?
C2 C3 C11 C12 55.1(2) . . . . ?
C2 C3 C11 C13 -68.4(2) . . . . ?
C3 C2 C10 C5 -15.2(2) . . . . ?
C3 C2 C10 C9 167.6(2) . . . . ?
C3 C4 C5 C6 -169.5(2) . . . . ?
C3 C4 C5 C10 13.8(2) . . . . ?
C4 C3 C11 O1 52.8(2) . . . . ?
C4 C3 C11 C12 -61.0(2) . . . . ?
C4 C3 C11 C13 175.6(2) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C4 C5 C10 C2 0.6(2) . . . . ?
C4 C5 C10 C9 178.13(19) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C5 C10 C2 -176.52(19) . . . . ?
C6 C5 C10 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C2 176.4(2) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C10 C2 C3 C4 22.7(2) . . . . ?
C10 C2 C3 C11 -98.1(2) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C11 C3 C4 C5 100.7(2) . . . . ?
C14 O1 C11 C3 62.7(3) . . . . ?
C14 O1 C11 C12 -177.9(2) . . . . ?
C14 O1 C11 C13 -61.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
