# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_cd15018
_database_code_depnum_ccdc_archive 'CCDC 2121251'
loop_
_audit_author_name
_audit_author_address
'Xinhong Yu'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br O2'
_chemical_formula_weight         357.23

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

_cell_length_a                   7.1586(8)
_cell_length_b                   11.9651(14)
_cell_length_c                   18.845(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1415
_cell_measurement_theta_min      5.503
_cell_measurement_theta_max      37.841

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.551
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9465
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3005
_reflns_number_gt                2135
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0253P)²] 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 701 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.011(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_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 -0.01159(9) 0.36152(6) 0.05895(3) 0.0774(3) Uani 1 1 d . . . . .
O1 O 0.4332(5) 0.2138(4) 0.3147(2) 0.0573(11) Uani 1 1 d . . . . .
O2 O 1.0524(5) 0.1566(4) 0.3222(2) 0.0665(12) Uani 1 1 d . . . . .
H2 H 1.1637 0.1624 0.3317 0.100 Uiso 1 1 calc R U . . .
C1 C 0.5178(8) 0.2860(5) 0.3452(3) 0.0443(12) Uani 1 1 d . . . . .
C2 C 0.4541(9) 0.3333(6) 0.4145(3) 0.0689(19) Uani 1 1 d . . . . .
H2A H 0.3480 0.2913 0.4321 0.083 Uiso 1 1 calc R U . . .
H2B H 0.4161 0.4105 0.4083 0.083 Uiso 1 1 calc R U . . .
C3 C 0.6131(10) 0.3266(7) 0.4665(3) 0.075(2) Uani 1 1 d . . . . .
H3A H 0.5721 0.3532 0.5125 0.090 Uiso 1 1 calc R U . . .
H3B H 0.6528 0.2495 0.4715 0.090 Uiso 1 1 calc R U . . .
C4 C 0.7738(8) 0.3966(5) 0.4408(3) 0.0546(15) Uani 1 1 d . . . . .
C5 C 0.8845(11) 0.4587(6) 0.4871(3) 0.071(2) Uani 1 1 d . . . . .
H5 H 0.8641 0.4530 0.5357 0.086 Uiso 1 1 calc R U . . .
C6 C 1.0199(12) 0.5265(6) 0.4633(4) 0.077(2) Uani 1 1 d . . . . .
H6 H 1.0916 0.5669 0.4956 0.092 Uiso 1 1 calc R U . . .
C7 C 1.0539(9) 0.5372(5) 0.3923(4) 0.071(2) Uani 1 1 d . . . . .
H7 H 1.1461 0.5856 0.3762 0.086 Uiso 1 1 calc R U . . .
C8 C 0.9502(8) 0.4753(5) 0.3448(3) 0.0556(16) Uani 1 1 d . . . . .
H8 H 0.9735 0.4826 0.2965 0.067 Uiso 1 1 calc R U . . .
C9 C 0.8111(7) 0.4021(5) 0.3679(3) 0.0420(14) Uani 1 1 d . . . . .
C10 C 0.7007(7) 0.3296(4) 0.3186(3) 0.0395(13) Uani 1 1 d . . . . .
C11 C 0.7080(7) 0.3486(5) 0.2368(3) 0.0393(12) Uani 1 1 d . . . . .
H11 H 0.7972 0.4067 0.2227 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7984(8) 0.2486(5) 0.2673(3) 0.0406(13) Uani 1 1 d . . . . .
H12 H 0.7285 0.1793 0.2590 0.049 Uiso 1 1 calc R U . . .
C13 C 1.0060(9) 0.2326(4) 0.2679(3) 0.0489(13) Uani 1 1 d . . . . .
H13A H 1.0475 0.2039 0.2225 0.059 Uiso 1 1 calc R U . . .
H13B H 1.0677 0.3036 0.2763 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5348(7) 0.3481(4) 0.1930(2) 0.0384(12) Uani 1 1 d . . . . .
C15 C 0.4803(10) 0.2569(4) 0.1538(3) 0.0501(14) Uani 1 1 d . . . . .
H15 H 0.5528 0.1924 0.1541 0.060 Uiso 1 1 calc R U . . .
C16 C 0.3177(8) 0.2604(5) 0.1137(3) 0.0512(15) Uani 1 1 d . . . . .
H16 H 0.2806 0.1983 0.0875 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2127(7) 0.3554(6) 0.1129(3) 0.0465(14) Uani 1 1 d . . . . .
C18 C 0.2658(8) 0.4488(5) 0.1505(3) 0.0535(16) Uani 1 1 d . . . . .
H18 H 0.1934 0.5133 0.1495 0.064 Uiso 1 1 calc R U . . .
C19 C 0.4283(8) 0.4449(5) 0.1899(3) 0.0499(15) Uani 1 1 d . . . . .
H19 H 0.4670 0.5081 0.2147 0.060 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 C17 1.901(5) . ?
O1 C1 1.201(6) . ?
O2 C13 1.408(6) . ?
O2 H2 0.8200 . ?
C1 C2 1.494(8) . ?
C1 C10 1.496(8) . ?
C2 C3 1.503(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.503(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.394(8) . ?
C4 C9 1.401(8) . ?
C5 C6 1.341(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.497(7) . ?
C10 C12 1.537(7) . ?
C10 C11 1.558(7) . ?
C11 C12 1.477(7) . ?
C11 C14 1.489(7) . ?
C11 H11 0.9800 . ?
C12 C13 1.499(9) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.375(7) . ?
C14 C19 1.388(7) . ?
C15 C16 1.389(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(8) . ?
C18 C19 1.381(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
C13 O2 H2 109.5 . . ?
O1 C1 C2 122.5(5) . . ?
O1 C1 C10 122.1(5) . . ?
C2 C1 C10 115.3(5) . . ?
C1 C2 C3 108.6(5) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 C2 109.9(5) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C9 118.8(6) . . ?
C5 C4 C3 122.0(6) . . ?
C9 C4 C3 119.2(5) . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 119.4(7) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 121.2(6) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 118.1(5) . . ?
C8 C9 C10 123.2(5) . . ?
C4 C9 C10 118.7(5) . . ?
C1 C10 C9 117.1(5) . . ?
C1 C10 C12 112.9(4) . . ?
C9 C10 C12 121.0(4) . . ?
C1 C10 C11 114.4(4) . . ?
C9 C10 C11 120.7(4) . . ?
C12 C10 C11 57.0(3) . . ?
C12 C11 C14 125.2(5) . . ?
C12 C11 C10 60.8(3) . . ?
C14 C11 C10 121.3(4) . . ?
C12 C11 H11 113.2 . . ?
C14 C11 H11 113.2 . . ?
C10 C11 H11 113.2 . . ?
C11 C12 C13 122.7(5) . . ?
C11 C12 C10 62.2(3) . . ?
C13 C12 C10 121.7(4) . . ?
C11 C12 H12 113.6 . . ?
C13 C12 H12 113.6 . . ?
C10 C12 H12 113.6 . . ?
O2 C13 C12 108.8(5) . . ?
O2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
O2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 C19 118.9(5) . . ?
C15 C14 C11 122.5(5) . . ?
C19 C14 C11 118.5(4) . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.5(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 Br1 120.2(4) . . ?
C18 C17 Br1 118.5(5) . . ?
C17 C18 C19 118.9(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 120.9(5) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

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
O1 C1 C2 C3 127.3(6) . . . . ?
C10 C1 C2 C3 -49.1(7) . . . . ?
C1 C2 C3 C4 62.5(7) . . . . ?
C2 C3 C4 C5 142.2(6) . . . . ?
C2 C3 C4 C9 -36.2(8) . . . . ?
C9 C4 C5 C6 2.7(10) . . . . ?
C3 C4 C5 C6 -175.6(7) . . . . ?
C4 C5 C6 C7 0.1(11) . . . . ?
C5 C6 C7 C8 -1.5(10) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 C4 2.7(9) . . . . ?
C7 C8 C9 C10 -177.2(5) . . . . ?
C5 C4 C9 C8 -4.0(8) . . . . ?
C3 C4 C9 C8 174.4(6) . . . . ?
C5 C4 C9 C10 175.9(5) . . . . ?
C3 C4 C9 C10 -5.7(8) . . . . ?
O1 C1 C10 C9 -168.1(5) . . . . ?
C2 C1 C10 C9 8.3(7) . . . . ?
O1 C1 C10 C12 -20.4(7) . . . . ?
C2 C1 C10 C12 156.0(5) . . . . ?
O1 C1 C10 C11 42.4(7) . . . . ?
C2 C1 C10 C11 -141.2(5) . . . . ?
C8 C9 C10 C1 -159.6(5) . . . . ?
C4 C9 C10 C1 20.4(7) . . . . ?
C8 C9 C10 C12 55.4(7) . . . . ?
C4 C9 C10 C12 -124.5(5) . . . . ?
C8 C9 C10 C11 -12.1(8) . . . . ?
C4 C9 C10 C11 167.9(5) . . . . ?
C1 C10 C11 C12 -102.4(5) . . . . ?
C9 C10 C11 C12 109.2(5) . . . . ?
C1 C10 C11 C14 13.2(7) . . . . ?
C9 C10 C11 C14 -135.1(5) . . . . ?
C12 C10 C11 C14 115.7(6) . . . . ?
C14 C11 C12 C13 138.9(5) . . . . ?
C10 C11 C12 C13 -111.6(5) . . . . ?
C14 C11 C12 C10 -109.5(5) . . . . ?
C1 C10 C12 C11 105.0(5) . . . . ?
C9 C10 C12 C11 -108.7(5) . . . . ?
C1 C10 C12 C13 -141.8(5) . . . . ?
C9 C10 C12 C13 4.5(8) . . . . ?
C11 C10 C12 C13 113.1(6) . . . . ?
C11 C12 C13 O2 157.3(5) . . . . ?
C10 C12 C13 O2 82.0(6) . . . . ?
C12 C11 C14 C15 -25.9(8) . . . . ?
C10 C11 C14 C15 -100.2(6) . . . . ?
C12 C11 C14 C19 156.5(5) . . . . ?
C10 C11 C14 C19 82.2(7) . . . . ?
C19 C14 C15 C16 -2.3(8) . . . . ?
C11 C14 C15 C16 -179.9(5) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C15 C16 C17 Br1 -179.4(4) . . . . ?
C16 C17 C18 C19 -0.2(9) . . . . ?
Br1 C17 C18 C19 179.9(4) . . . . ?
C17 C18 C19 C14 -1.5(9) . . . . ?
C15 C14 C19 C18 2.7(8) . . . . ?
C11 C14 C19 C18 -179.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 O2 0.93 2.51 3.411(7) 162.1 3_655
O2 H2 O1 0.82 2.05 2.814(5) 155.0 1_655

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



