# 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. 
# 
#######################################################################

data_cu_asm599_1_a
_database_code_depnum_ccdc_archive 'CCDC 2493459'
loop_
_audit_author_name
_audit_author_address
'Anton Makarov'
;King Abdullah University of Science and Technology
Saudi Arabia
;
_audit_update_record             
;
2025-10-06 deposited with the CCDC.	2026-05-21 downloaded from the CCDC.
;
_audit_creation_date             2025-10-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1-phenyl-2-oxabicyclo[2.1.1]hexan-3-one
_chemical_formula_moiety         'C11 H10 O2'
_chemical_formula_sum            'C11 H10 O2'
_chemical_formula_weight         174.19
_chemical_melting_point          333
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5720(2)
_cell_length_b                   5.5244(2)
_cell_length_c                   20.5726(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.6180(10)
_cell_angle_gamma                90
_cell_volume                     858.85(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      5.86
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         5.855
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1465
_reflns_number_total             1563
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.032
_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)+(0.0396P)²+0.3390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.26432(12) 0.56520(16) 0.48370(4) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.26452(15) 0.4156(2) 0.52619(5) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.26658(10) 0.47298(14) 0.59108(4) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.26433(14) 0.22691(19) 0.62141(5) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.26175(13) 0.24304(19) 0.69360(5) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.33490(14) 0.0559(2) 0.73190(5) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.393620 -0.074224 0.712131 0.026 Uiso 1 1 calc R U . . .
C5 C 0.32205(15) 0.0594(2) 0.79906(6) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.371053 -0.069324 0.824982 0.030 Uiso 1 1 calc R U . . .
C6 C 0.23816(15) 0.2495(2) 0.82826(6) 0.0258(3) Uani 1 1 d . . . . .
H6 H 0.228590 0.250561 0.874084 0.031 Uiso 1 1 calc R U . . .
C7 C 0.16813(15) 0.4384(2) 0.79048(6) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.112413 0.570346 0.810579 0.031 Uiso 1 1 calc R U . . .
C8 C 0.17913(14) 0.4354(2) 0.72333(5) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.130230 0.564671 0.697613 0.027 Uiso 1 1 calc R U . . .
C9 C 0.40268(14) 0.0939(2) 0.58276(5) 0.0216(3) Uani 1 1 d . . . . .
H9A H 0.420303 -0.078920 0.594188 0.026 Uiso 1 1 calc R U . . .
H9B H 0.516334 0.180481 0.579788 0.026 Uiso 1 1 calc R U . . .
C10 C 0.26177(15) 0.1434(2) 0.52546(5) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.2612(17) 0.064(3) 0.4843(7) 0.026(3) Uiso 1 1 d . . . . .
C11 C 0.12042(14) 0.1017(2) 0.57643(5) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.009480 0.194954 0.568552 0.026 Uiso 1 1 calc R U . . .
H11B H 0.097651 -0.069935 0.586910 0.026 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
O1 C1 1.2029(14) . ?
C1 O2 1.3711(13) . ?
C1 C10 1.5039(16) . ?
O2 C2 1.4963(13) . ?
C2 C3 1.4891(15) . ?
C2 C9 1.5411(14) . ?
C2 C11 1.5475(14) . ?
C3 C4 1.3934(15) . ?
C3 C8 1.3937(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3913(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3842(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3865(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3894(16) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5635(15) . ?
C10 H10 0.955(14) . ?
C10 C11 1.5620(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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 123.24(11) . . ?
O1 C1 C10 132.86(11) . . ?
O2 C1 C10 103.90(9) . . ?
C1 O2 C2 101.32(8) . . ?
O2 C2 C9 101.08(8) . . ?
O2 C2 C10 78.47(6) . . ?
O2 C2 C11 100.53(8) . . ?
C3 C2 O2 111.27(8) . . ?
C3 C2 C9 126.53(9) . . ?
C3 C2 C10 170.19(9) . . ?
C3 C2 C11 124.76(9) . . ?
C9 C2 C10 49.74(6) . . ?
C9 C2 C11 87.38(8) . . ?
C11 C2 C10 49.65(6) . . ?
C4 C3 C2 119.32(9) . . ?
C4 C3 C8 119.41(10) . . ?
C8 C3 C2 121.18(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.07(10) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(11) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.84(11) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.24(11) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.14(10) . . ?
C7 C8 H8 119.9 . . ?
C2 C9 H9A 115.0 . . ?
C2 C9 H9B 115.0 . . ?
C2 C9 C10 81.48(8) . . ?
H9A C9 H9B 112.1 . . ?
C10 C9 H9A 115.0 . . ?
C10 C9 H9B 115.0 . . ?
C1 C10 C2 76.31(7) . . ?
C1 C10 C9 99.16(9) . . ?
C1 C10 H10 118.1(8) . . ?
C1 C10 C11 98.65(9) . . ?
C2 C10 H10 165.6(8) . . ?
C9 C10 C2 48.78(6) . . ?
C9 C10 H10 123.5(8) . . ?
C11 C10 C2 49.03(6) . . ?
C11 C10 C9 86.09(8) . . ?
C11 C10 H10 124.2(8) . . ?
C2 C11 C10 81.32(8) . . ?
C2 C11 H11A 115.1 . . ?
C2 C11 H11B 115.1 . . ?
C10 C11 H11A 115.1 . . ?
C10 C11 H11B 115.1 . . ?
H11A C11 H11B 112.1 . . ?

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 O2 C2 179.55(11) . . . . ?
O1 C1 C10 C2 -179.54(14) . . . . ?
O1 C1 C10 C9 137.03(13) . . . . ?
O1 C1 C10 C11 -135.56(13) . . . . ?
C1 O2 C2 C3 -178.66(8) . . . . ?
C1 O2 C2 C9 44.70(9) . . . . ?
C1 O2 C2 C10 0.10(7) . . . . ?
C1 O2 C2 C11 -44.66(9) . . . . ?
C1 C10 C11 C2 -63.31(9) . . . . ?
O2 C1 C10 C2 0.10(7) . . . . ?
O2 C1 C10 C9 -43.33(10) . . . . ?
O2 C1 C10 C11 44.07(10) . . . . ?
O2 C2 C3 C4 -152.05(9) . . . . ?
O2 C2 C3 C8 31.45(13) . . . . ?
O2 C2 C9 C10 -64.36(8) . . . . ?
O2 C2 C11 C10 64.87(8) . . . . ?
C2 C3 C4 C5 -175.25(10) . . . . ?
C2 C3 C8 C7 175.71(10) . . . . ?
C2 C9 C10 C1 62.62(9) . . . . ?
C2 C9 C10 C11 -35.53(8) . . . . ?
C3 C2 C9 C10 168.41(11) . . . . ?
C3 C2 C11 C10 -169.82(10) . . . . ?
C3 C4 C5 C6 -0.61(17) . . . . ?
C4 C3 C8 C7 -0.79(16) . . . . ?
C4 C5 C6 C7 -0.61(17) . . . . ?
C5 C6 C7 C8 1.13(17) . . . . ?
C6 C7 C8 C3 -0.43(16) . . . . ?
C8 C3 C4 C5 1.30(16) . . . . ?
C9 C2 C3 C4 -29.03(15) . . . . ?
C9 C2 C3 C8 154.47(11) . . . . ?
C9 C2 C11 C10 -35.91(8) . . . . ?
C9 C10 C11 C2 35.37(7) . . . . ?
C10 C1 O2 C2 -0.14(10) . . . . ?
C11 C2 C3 C4 87.37(13) . . . . ?
C11 C2 C3 C8 -89.13(13) . . . . ?
C11 C2 C9 C10 35.86(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF, n-hexane'
_chemical_properties_physical    acid-sensitive
####################################################################### 
# 
# 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_cu_asm5622_0m
_database_code_depnum_ccdc_archive 'CCDC 2493461'
loop_
_audit_author_name
_audit_author_address
'Anton Makarov'
;KAUST
Saudi Arabia
;
_audit_update_record             
;
2025-10-06 deposited with the CCDC.	2026-05-21 downloaded from the CCDC.
;
_audit_creation_date             2025-10-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-bromo-1-phenyl-2-oxabicyclo[2.1.1]hexan-3-one
_chemical_formula_moiety         'C11 H9 Br O2'
_chemical_formula_sum            'C11 H9 Br O2'
_chemical_formula_weight         253.09
_chemical_melting_point          353
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3703(2)
_cell_length_b                   9.0082(3)
_cell_length_c                   9.2840(3)
_cell_angle_alpha                69.2060(10)
_cell_angle_beta                 80.6720(10)
_cell_angle_gamma                88.2460(10)
_cell_volume                     491.26(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      68.02
_cell_measurement_theta_min      5.16
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.611
_exptl_absorpt_coefficient_mu    5.456
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.4673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.6206.
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    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prisms
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25934
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.060
_diffrn_reflns_theta_min         5.164
_diffrn_ambient_temperature      120.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1779
_reflns_number_total             1781
_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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0193
_refine_ls_restrained_S_all      1.114
_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)+(0.0107P)²+0.5876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0457
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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
O1 O 0.93977(19) 0.63830(15) 0.63679(15) 0.0177(3) Uani 1 1 d . . . . .
C1 C 1.0146(3) 0.7647(2) 0.5064(2) 0.0170(4) Uani 1 1 d . . . . .
Br1 Br 0.85325(3) 1.00375(2) 0.24771(2) 0.02226(8) Uani 1 1 d . . . . .
O2 O 1.1967(2) 0.80839(16) 0.46482(16) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.8148(3) 0.8244(2) 0.4378(2) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.7117(3) 0.6644(2) 0.4543(2) 0.0161(4) Uani 1 1 d . . . . .
H3A H 0.807078 0.593942 0.414412 0.019 Uiso 1 1 calc R U . . .
H3B H 0.570682 0.672124 0.420799 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7065(3) 0.6392(2) 0.6290(2) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.6602(3) 0.8176(2) 0.5886(2) 0.0158(4) Uani 1 1 d . . . . .
H5A H 0.715471 0.868512 0.654004 0.019 Uiso 1 1 calc R U . . .
H5B H 0.511901 0.846665 0.573995 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5913(3) 0.5037(2) 0.7593(2) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.6885(3) 0.3571(2) 0.8116(2) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.832603 0.346777 0.770740 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5747(3) 0.2272(2) 0.9226(2) 0.0241(4) Uani 1 1 d . . . . .
H8 H 0.640609 0.127500 0.957379 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3652(3) 0.2418(2) 0.9835(2) 0.0252(4) Uani 1 1 d . . . . .
H9 H 0.287483 0.152120 1.059520 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2687(3) 0.3873(2) 0.9335(2) 0.0245(4) Uani 1 1 d . . . . .
H10 H 0.125307 0.397361 0.976110 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3814(3) 0.5185(2) 0.8212(2) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.314947 0.618047 0.786938 0.023 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
O1 C1 1.363(2) . ?
O1 C4 1.499(2) . ?
C1 O2 1.193(2) . ?
C1 C2 1.514(2) . ?
Br1 C2 1.9089(17) . ?
C2 C3 1.549(2) . ?
C2 C5 1.559(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.550(2) . ?
C4 C5 1.546(2) . ?
C4 C6 1.487(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.398(3) . ?
C6 C11 1.390(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?

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
C1 O1 C4 101.58(13) . . ?
O1 C1 C2 102.64(14) . . ?
O2 C1 O1 124.96(17) . . ?
O2 C1 C2 132.39(17) . . ?
C1 C2 Br1 115.80(12) . . ?
C1 C2 C3 99.84(14) . . ?
C1 C2 C4 77.09(11) . . ?
C1 C2 C5 99.97(14) . . ?
Br1 C2 C4 167.09(11) . . ?
C3 C2 Br1 123.21(12) . . ?
C3 C2 C4 49.95(9) . . ?
C3 C2 C5 87.58(13) . . ?
C5 C2 Br1 124.38(12) . . ?
C5 C2 C4 49.72(9) . . ?
C2 C3 H3A 115.2 . . ?
C2 C3 H3B 115.2 . . ?
C2 C3 C4 80.14(12) . . ?
H3A C3 H3B 112.3 . . ?
C4 C3 H3A 115.2 . . ?
C4 C3 H3B 115.2 . . ?
O1 C4 C2 78.69(10) . . ?
O1 C4 C3 100.92(13) . . ?
O1 C4 C5 101.39(13) . . ?
C3 C4 C2 49.90(9) . . ?
C5 C4 C2 50.31(9) . . ?
C5 C4 C3 88.02(13) . . ?
C6 C4 O1 111.04(14) . . ?
C6 C4 C2 169.96(14) . . ?
C6 C4 C3 123.41(15) . . ?
C6 C4 C5 127.03(15) . . ?
C2 C5 H5A 115.3 . . ?
C2 C5 H5B 115.3 . . ?
C4 C5 C2 79.96(12) . . ?
C4 C5 H5A 115.3 . . ?
C4 C5 H5B 115.3 . . ?
H5A C5 H5B 112.3 . . ?
C7 C6 C4 119.94(16) . . ?
C11 C6 C4 120.18(16) . . ?
C11 C6 C7 119.69(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.97(18) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.29(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.02(18) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.15(18) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 119.87(17) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

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 Br1 -179.28(11) . . . . ?
O1 C1 C2 C3 -44.75(16) . . . . ?
O1 C1 C2 C4 0.05(12) . . . . ?
O1 C1 C2 C5 44.51(16) . . . . ?
O1 C4 C5 C2 64.72(13) . . . . ?
O1 C4 C6 C7 -36.1(2) . . . . ?
O1 C4 C6 C11 148.93(15) . . . . ?
C1 O1 C4 C2 0.05(12) . . . . ?
C1 O1 C4 C3 45.01(15) . . . . ?
C1 O1 C4 C5 -45.16(15) . . . . ?
C1 O1 C4 C6 177.47(14) . . . . ?
C1 C2 C3 C4 63.78(13) . . . . ?
C1 C2 C5 C4 -63.50(13) . . . . ?
Br1 C2 C3 C4 -166.32(13) . . . . ?
Br1 C2 C5 C4 165.52(14) . . . . ?
O2 C1 C2 Br1 0.1(3) . . . . ?
O2 C1 C2 C3 134.6(2) . . . . ?
O2 C1 C2 C4 179.4(2) . . . . ?
O2 C1 C2 C5 -136.1(2) . . . . ?
C2 C3 C4 O1 -64.94(13) . . . . ?
C2 C3 C4 C5 36.27(12) . . . . ?
C2 C3 C4 C6 170.63(17) . . . . ?
C2 C4 C6 C7 129.3(8) . . . . ?
C2 C4 C6 C11 -45.7(9) . . . . ?
C3 C2 C5 C4 36.06(12) . . . . ?
C3 C4 C5 C2 -36.02(12) . . . . ?
C3 C4 C6 C7 83.7(2) . . . . ?
C3 C4 C6 C11 -91.3(2) . . . . ?
C4 O1 C1 O2 -179.51(17) . . . . ?
C4 O1 C1 C2 -0.06(16) . . . . ?
C4 C6 C7 C8 -174.06(17) . . . . ?
C4 C6 C11 C10 174.38(17) . . . . ?
C5 C2 C3 C4 -35.92(12) . . . . ?
C5 C4 C6 C7 -159.80(17) . . . . ?
C5 C4 C6 C11 25.2(3) . . . . ?
C6 C4 C5 C2 -167.64(17) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C6 C11 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
_chemical_properties_physical    acid-sensitive
