# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_O42AAB104_0m
_database_code_depnum_ccdc_archive 'CCDC 2226509'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Br O3'
_chemical_formula_sum            'C17 H19 Br O3'
_chemical_formula_weight         351.23

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'
O O 0.0106 0.0060 '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'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.3235(17)
_cell_length_b                   9.838(2)
_cell_length_c                   17.181(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.24

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    2.616
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38606
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4799
_reflns_number_gt                4258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.991

_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.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²+0.3265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1687 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4799
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.06428(3) 0.68501(3) 0.43498(2) 0.02603(7) Uani 1 1 d . . . . .
O1 O 0.86864(19) 0.13410(19) 0.64680(10) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.44552(17) 0.18557(18) 0.71451(8) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.96754(17) 0.1953(2) 0.76046(10) 0.0286(4) Uani 1 1 d . . . . .
C1 C 0.9826(3) 0.0356(3) 0.63790(17) 0.0337(7) Uani 1 1 d . . . . .
H1 H 1.075238 0.082549 0.636992 0.051 Uiso 1 1 calc R U . . .
H13 H 0.969312 -0.014240 0.589031 0.051 Uiso 1 1 calc R U . . .
H14 H 0.980333 -0.028325 0.681634 0.051 Uiso 1 1 calc R U . . .
C2 C 0.8738(2) 0.2076(2) 0.71229(13) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.7505(2) 0.3043(3) 0.71905(12) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.6669(2) 0.3359(2) 0.64515(12) 0.0141(4) Uani 1 1 d . . . . .
H3 H 0.649161 0.247955 0.617555 0.017 Uiso 1 1 calc R U . . .
C5 C 0.7599(2) 0.4240(2) 0.59235(12) 0.0140(4) Uani 1 1 d . . . . .
C6 C 0.7923(3) 0.3825(2) 0.51701(13) 0.0185(4) Uani 1 1 d . . . . .
H2 H 0.752839 0.300045 0.497804 0.022 Uiso 1 1 calc R U . . .
C7 C 0.8818(3) 0.4598(3) 0.46893(14) 0.0207(5) Uani 1 1 d . . . . .
H19 H 0.903965 0.430282 0.417674 0.025 Uiso 1 1 calc R U . . .
C8 C 0.9371(3) 0.5800(2) 0.49769(12) 0.0184(4) Uani 1 1 d . . . . .
C9 C 0.5203(2) 0.4015(2) 0.66160(12) 0.0143(4) Uani 1 1 d . . . . .
H4 H 0.535522 0.485053 0.693719 0.017 Uiso 1 1 calc R U . . .
C10 C 0.4204(2) 0.3063(3) 0.70543(11) 0.0158(4) Uani 1 1 d . . . . .
C11 C 0.2797(2) 0.3695(3) 0.72878(14) 0.0213(5) Uani 1 1 d . . . . .
H12 H 0.296750 0.450158 0.761960 0.026 Uiso 1 1 calc R U . . .
H11 H 0.221492 0.303399 0.758636 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2000(2) 0.4113(3) 0.65393(14) 0.0227(5) Uani 1 1 d . . . . .
H10 H 0.174574 0.329026 0.623796 0.027 Uiso 1 1 calc R U . . .
H5 H 0.110064 0.458956 0.667819 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2932(3) 0.5045(3) 0.60394(15) 0.0234(5) Uani 1 1 d . . . . .
H6 H 0.306898 0.592094 0.631347 0.028 Uiso 1 1 calc R U . . .
H7 H 0.243044 0.523432 0.554321 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4405(2) 0.4417(2) 0.58635(12) 0.0178(4) Uani 1 1 d . . . . .
H8 H 0.499188 0.507946 0.556892 0.021 Uiso 1 1 calc R U . . .
H9 H 0.427575 0.360130 0.553360 0.021 Uiso 1 1 calc R U . . .
C15 C 0.7259(2) 0.3585(2) 0.78832(13) 0.0198(5) Uani 1 1 d . . . . .
H15 H 0.785467 0.335551 0.831211 0.024 Uiso 1 1 calc R U . . .
H16 H 0.648639 0.420330 0.795125 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8170(2) 0.5458(2) 0.61908(13) 0.0172(4) Uani 1 1 d . . . . .
H17 H 0.795203 0.575520 0.670334 0.021 Uiso 1 1 calc R U . . .
C17 C 0.9056(2) 0.6250(2) 0.57219(13) 0.0185(4) Uani 1 1 d . . . . .
H18 H 0.943630 0.708417 0.590910 0.022 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 C8 1.906(2) . ?
O1 C2 1.339(3) . ?
O1 C1 1.446(3) . ?
O2 C10 1.220(3) . ?
O3 C2 1.210(3) . ?
C1 H1 0.9800 . ?
C1 H13 0.9800 . ?
C1 H14 0.9800 . ?
C2 C3 1.496(3) . ?
C3 C15 1.324(3) . ?
C3 C4 1.522(3) . ?
C4 C5 1.526(3) . ?
C4 C9 1.538(3) . ?
C4 H3 1.0000 . ?
C5 C16 1.389(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.399(3) . ?
C6 H2 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H19 0.9500 . ?
C8 C17 1.386(3) . ?
C9 C10 1.520(3) . ?
C9 C14 1.543(3) . ?
C9 H4 1.0000 . ?
C10 C11 1.507(3) . ?
C11 C12 1.541(3) . ?
C11 H12 0.9900 . ?
C11 H11 0.9900 . ?
C12 C13 1.527(3) . ?
C12 H10 0.9900 . ?
C12 H5 0.9900 . ?
C13 C14 1.536(3) . ?
C13 H6 0.9900 . ?
C13 H7 0.9900 . ?
C14 H8 0.9900 . ?
C14 H9 0.9900 . ?
C15 H15 0.9500 . ?
C15 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C16 H17 0.9500 . ?
C17 H18 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
C2 O1 C1 115.1(2) . . ?
O1 C1 H1 109.5 . . ?
O1 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
O1 C1 H14 109.5 . . ?
H1 C1 H14 109.5 . . ?
H13 C1 H14 109.5 . . ?
O3 C2 O1 123.2(2) . . ?
O3 C2 C3 124.4(2) . . ?
O1 C2 C3 112.38(18) . . ?
C15 C3 C2 117.3(2) . . ?
C15 C3 C4 125.4(2) . . ?
C2 C3 C4 117.30(19) . . ?
C3 C4 C5 108.71(17) . . ?
C3 C4 C9 112.82(17) . . ?
C5 C4 C9 112.08(17) . . ?
C3 C4 H3 107.7 . . ?
C5 C4 H3 107.7 . . ?
C9 C4 H3 107.7 . . ?
C16 C5 C6 118.5(2) . . ?
C16 C5 C4 120.8(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H2 119.3 . . ?
C7 C6 H2 119.3 . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 H19 120.8 . . ?
C6 C7 H19 120.8 . . ?
C7 C8 C17 121.6(2) . . ?
C7 C8 Br1 119.61(17) . . ?
C17 C8 Br1 118.73(17) . . ?
C10 C9 C4 112.10(18) . . ?
C10 C9 C14 106.12(17) . . ?
C4 C9 C14 112.47(17) . . ?
C10 C9 H4 108.7 . . ?
C4 C9 H4 108.7 . . ?
C14 C9 H4 108.7 . . ?
O2 C10 C11 122.3(2) . . ?
O2 C10 C9 123.07(19) . . ?
C11 C10 C9 114.3(2) . . ?
C10 C11 C12 107.92(19) . . ?
C10 C11 H12 110.1 . . ?
C12 C11 H12 110.1 . . ?
C10 C11 H11 110.1 . . ?
C12 C11 H11 110.1 . . ?
H12 C11 H11 108.4 . . ?
C13 C12 C11 110.8(2) . . ?
C13 C12 H10 109.5 . . ?
C11 C12 H10 109.5 . . ?
C13 C12 H5 109.5 . . ?
C11 C12 H5 109.5 . . ?
H10 C12 H5 108.1 . . ?
C12 C13 C14 112.2(2) . . ?
C12 C13 H6 109.2 . . ?
C14 C13 H6 109.2 . . ?
C12 C13 H7 109.2 . . ?
C14 C13 H7 109.2 . . ?
H6 C13 H7 107.9 . . ?
C13 C14 C9 111.67(18) . . ?
C13 C14 H8 109.3 . . ?
C9 C14 H8 109.3 . . ?
C13 C14 H9 109.3 . . ?
C9 C14 H9 109.3 . . ?
H8 C14 H9 107.9 . . ?
C3 C15 H15 120.0 . . ?
C3 C15 H16 120.0 . . ?
H15 C15 H16 120.0 . . ?
C5 C16 C17 121.3(2) . . ?
C5 C16 H17 119.4 . . ?
C17 C16 H17 119.4 . . ?
C8 C17 C16 118.8(2) . . ?
C8 C17 H18 120.6 . . ?
C16 C17 H18 120.6 . . ?

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
C1 O1 C2 O3 1.1(3) . . . . ?
C1 O1 C2 C3 -178.1(2) . . . . ?
O3 C2 C3 C15 -14.6(4) . . . . ?
O1 C2 C3 C15 164.6(2) . . . . ?
O3 C2 C3 C4 163.3(2) . . . . ?
O1 C2 C3 C4 -17.4(3) . . . . ?
C15 C3 C4 C5 106.4(2) . . . . ?
C2 C3 C4 C5 -71.3(3) . . . . ?
C15 C3 C4 C9 -18.5(3) . . . . ?
C2 C3 C4 C9 163.69(19) . . . . ?
C3 C4 C5 C16 -55.6(3) . . . . ?
C9 C4 C5 C16 69.8(2) . . . . ?
C3 C4 C5 C6 122.9(2) . . . . ?
C9 C4 C5 C6 -111.8(2) . . . . ?
C16 C5 C6 C7 0.9(3) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C17 -0.2(4) . . . . ?
C6 C7 C8 Br1 178.02(17) . . . . ?
C3 C4 C9 C10 -64.2(2) . . . . ?
C5 C4 C9 C10 172.66(17) . . . . ?
C3 C4 C9 C14 176.27(19) . . . . ?
C5 C4 C9 C14 53.2(2) . . . . ?
C4 C9 C10 O2 -11.5(3) . . . . ?
C14 C9 C10 O2 111.7(2) . . . . ?
C4 C9 C10 C11 175.27(18) . . . . ?
C14 C9 C10 C11 -61.6(2) . . . . ?
O2 C10 C11 C12 -111.5(2) . . . . ?
C9 C10 C11 C12 61.8(2) . . . . ?
C10 C11 C12 C13 -55.3(3) . . . . ?
C11 C12 C13 C14 54.0(3) . . . . ?
C12 C13 C14 C9 -55.3(3) . . . . ?
C10 C9 C14 C13 56.0(2) . . . . ?
C4 C9 C14 C13 178.89(19) . . . . ?
C6 C5 C16 C17 -0.4(3) . . . . ?
C4 C5 C16 C17 178.06(19) . . . . ?
C7 C8 C17 C16 0.7(3) . . . . ?
Br1 C8 C17 C16 -177.59(16) . . . . ?
C5 C16 C17 C8 -0.4(3) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.061



