# 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_scd23_133_0m
_database_code_depnum_ccdc_archive 'CCDC 2300659'
loop_
_audit_author_name
_audit_author_address
'Antonio Galdamez'
;Facultad de Ciencias,  Universidad de Chile
Chile
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2023-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br O4'
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_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      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                   5.7333(3)
_cell_length_b                   15.4063(8)
_cell_length_c                   16.4742(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.990(2)
_cell_angle_gamma                90
_cell_volume                     1451.62(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.628
_cell_measurement_theta_min      2.644
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.4990
_exptl_absorpt_correction_T_min  0.2969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.5950.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.798
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.028
_diffrn_reflns_theta_min         1.812
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.798
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2606
_reflns_number_total             6307
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         6307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.005
_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)+(0.0530P)²+1.0254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1577
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.72326(8) 0.15283(3) 0.00780(2) 0.07829(19) Uani 1 1 d . . . . .
O1 O 0.2733(3) 0.04732(12) -0.31438(11) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.1892(3) 0.12596(17) -0.61239(13) 0.0590(6) Uani 1 1 d . . . . .
O3 O -0.1546(3) 0.14804(14) -0.56093(13) 0.0538(5) Uani 1 1 d . . . . .
O4 O 0.9940(4) 0.24588(16) -0.29396(15) 0.0641(6) Uani 1 1 d . . . . .
C1 C 0.5764(5) 0.11757(19) -0.09354(17) 0.0460(7) Uani 1 1 d . . . . .
C2 C 0.3627(6) 0.0761(2) -0.09490(18) 0.0513(7) Uani 1 1 d . . . . .
H2 H 0.292957 0.065482 -0.046573 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2532(5) 0.05051(19) -0.16801(18) 0.0477(7) Uani 1 1 d . . . . .
H3 H 0.109861 0.022056 -0.170030 0.057 Uiso 1 1 calc R U . . .
C4 C 0.3616(4) 0.06820(16) -0.23781(16) 0.0356(6) Uani 1 1 d . . . . .
C5 C 0.5746(4) 0.11037(16) -0.23671(15) 0.0321(5) Uani 1 1 d . . . . .
C6 C 0.6845(5) 0.13609(17) -0.16376(16) 0.0400(6) Uani 1 1 d . . . . .
H6 H 0.827152 0.165026 -0.161849 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6381(4) 0.12273(17) -0.32310(15) 0.0335(5) Uani 1 1 d . . . . .
H7 H 0.795(5) 0.1095(17) -0.3279(15) 0.030(6) Uiso 1 1 d . . . . .
C8 C 0.4634(4) 0.05919(18) -0.36784(16) 0.0374(6) Uani 1 1 d . . . . .
H8 H 0.538(4) 0.0027(19) -0.3707(16) 0.037(7) Uiso 1 1 d . . . . .
C9 C 0.3683(4) 0.08480(17) -0.45006(15) 0.0365(6) Uani 1 1 d . . . . .
H9 H 0.474664 0.090830 -0.489822 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1481(4) 0.09979(19) -0.47204(17) 0.0427(6) Uani 1 1 d . . . . .
H10 H 0.037552 0.094341 -0.433621 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0702(4) 0.12503(19) -0.55583(17) 0.0410(6) Uani 1 1 d . . . . .
C12 C -0.2507(5) 0.1757(2) -0.6401(2) 0.0556(8) Uani 1 1 d . . . . .
H12A H -0.219420 0.132407 -0.679817 0.083 Uiso 1 1 calc R U . . .
H12B H -0.179945 0.229594 -0.654223 0.083 Uiso 1 1 calc R U . . .
H12C H -0.416527 0.183443 -0.638823 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6100(4) 0.21693(17) -0.35010(16) 0.0382(6) Uani 1 1 d . . . . .
H13A H 0.598581 0.219001 -0.409096 0.046 Uiso 1 1 calc R U . . .
H13B H 0.464760 0.239301 -0.331588 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8079(5) 0.27507(19) -0.31856(16) 0.0422(6) Uani 1 1 d . . . . .
C15 C 0.7636(7) 0.3699(2) -0.3212(2) 0.0656(9) Uani 1 1 d . . . . .
H15A H 0.675514 0.384379 -0.371084 0.098 Uiso 1 1 calc R U . . .
H15B H 0.909926 0.400394 -0.318417 0.098 Uiso 1 1 calc R U . . .
H15C H 0.676590 0.386276 -0.275916 0.098 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 1.896(3) . ?
O1 C4 1.364(3) . ?
O1 C8 1.460(3) . ?
O2 C11 1.193(3) . ?
O3 C11 1.334(3) . ?
O3 C12 1.444(4) . ?
O4 C14 1.202(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.380(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(4) . ?
C4 C5 1.382(3) . ?
C5 C6 1.376(4) . ?
C5 C7 1.506(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.93(3) . ?
C7 C8 1.550(4) . ?
C7 C13 1.523(4) . ?
C8 H8 0.97(3) . ?
C8 C9 1.478(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.310(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.473(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(4) . ?
C14 C15 1.483(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C4 O1 C8 106.49(18) . . ?
C11 O3 C12 116.2(2) . . ?
C2 C1 Br1 119.1(2) . . ?
C6 C1 Br1 118.7(2) . . ?
C6 C1 C2 122.1(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
O1 C4 C3 124.6(2) . . ?
O1 C4 C5 113.2(2) . . ?
C3 C4 C5 122.3(2) . . ?
C4 C5 C7 108.6(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C7 131.5(2) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 H6 121.1 . . ?
C5 C7 H7 110.6(15) . . ?
C5 C7 C8 100.3(2) . . ?
C5 C7 C13 111.7(2) . . ?
C8 C7 H7 114.7(16) . . ?
C13 C7 H7 105.5(16) . . ?
C13 C7 C8 114.3(2) . . ?
O1 C8 C7 106.1(2) . . ?
O1 C8 H8 105.6(16) . . ?
O1 C8 C9 110.1(2) . . ?
C7 C8 H8 108.3(15) . . ?
C9 C8 C7 116.9(2) . . ?
C9 C8 H8 109.3(16) . . ?
C8 C9 H9 117.0 . . ?
C10 C9 C8 126.0(2) . . ?
C10 C9 H9 117.0 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 121.9(2) . . ?
C11 C10 H10 119.0 . . ?
O2 C11 O3 123.4(3) . . ?
O2 C11 C10 125.6(2) . . ?
O3 C11 C10 111.0(2) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 108.8 . . ?
C7 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C7 113.8(2) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
O4 C14 C13 121.5(3) . . ?
O4 C14 C15 121.7(3) . . ?
C15 C14 C13 116.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 179.6(2) . . . . ?
Br1 C1 C6 C5 -179.66(19) . . . . ?
O1 C4 C5 C6 179.5(2) . . . . ?
O1 C4 C5 C7 2.0(3) . . . . ?
O1 C8 C9 C10 3.6(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C3 C4 O1 -179.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C7 -177.6(2) . . . . ?
C4 O1 C8 C7 -22.2(3) . . . . ?
C4 O1 C8 C9 -149.5(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C7 C8 -14.9(3) . . . . ?
C4 C5 C7 C13 106.6(2) . . . . ?
C5 C7 C8 O1 22.1(2) . . . . ?
C5 C7 C8 C9 145.3(2) . . . . ?
C5 C7 C13 C14 78.2(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C5 C7 C8 168.0(3) . . . . ?
C6 C5 C7 C13 -70.6(3) . . . . ?
C7 C5 C6 C1 177.5(3) . . . . ?
C7 C8 C9 C10 -117.5(3) . . . . ?
C7 C13 C14 O4 18.7(4) . . . . ?
C7 C13 C14 C15 -162.7(3) . . . . ?
C8 O1 C4 C3 -167.4(3) . . . . ?
C8 O1 C4 C5 13.1(3) . . . . ?
C8 C7 C13 C14 -168.8(2) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 O2 7.8(5) . . . . ?
C9 C10 C11 O3 -171.6(3) . . . . ?
C12 O3 C11 O2 -0.5(4) . . . . ?
C12 O3 C11 C10 179.0(3) . . . . ?
C13 C7 C8 O1 -97.4(2) . . . . ?
C13 C7 C8 C9 25.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
