# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20201012xsy_0m
_database_code_depnum_ccdc_archive 'CCDC 2061494'
loop_
_audit_author_name
_audit_author_address
'ShuSheng Zhang'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2021-02-06 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 Br O2'
_chemical_formula_weight         289.12

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                   6.2023(13)
_cell_length_b                   11.202(2)
_cell_length_c                   16.755(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1164.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    2761
_cell_measurement_theta_min      2.1870
_cell_measurement_theta_max      27.6531

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.516
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8116
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.0564
_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       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2836
_reflns_number_gt                1585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.984

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0069P)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 480 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2836
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 0.68403(11) 0.97652(4) 0.50495(5) 0.0822(3) Uani 1 1 d . . . . .
O1 O 0.2811(6) 0.5697(3) 0.7724(2) 0.0524(10) Uani 1 1 d . . . . .
O2 O -0.0341(7) 0.4784(4) 0.7929(3) 0.0725(13) Uani 1 1 d . . . . .
C1 C 0.6192(9) 0.8484(4) 0.5749(4) 0.0516(15) Uani 1 1 d . . . . .
C2 C 0.4182(9) 0.8415(4) 0.6094(4) 0.0555(16) Uani 1 1 d . . . . .
H3 H 0.315694 0.900312 0.599534 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3700(8) 0.7455(4) 0.6592(3) 0.0465(14) Uani 1 1 d . . . . .
H4 H 0.234243 0.739907 0.682448 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5221(8) 0.6591(4) 0.6740(3) 0.0427(13) Uani 1 1 d . . . . .
C5 C 0.4763(9) 0.5509(4) 0.7260(4) 0.0450(14) Uani 1 1 d . . . . .
H8 H 0.597742 0.538432 0.762521 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4340(9) 0.4376(4) 0.6809(3) 0.0449(14) Uani 1 1 d . . . . .
C7 C 0.2324(9) 0.3958(4) 0.7020(4) 0.0473(14) Uani 1 1 d . . . . .
C8 C 0.1484(10) 0.2912(4) 0.6696(4) 0.0627(18) Uani 1 1 d . . . . .
H7 H 0.011705 0.263913 0.683224 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2759(14) 0.2305(5) 0.6169(4) 0.081(2) Uani 1 1 d . . . . .
H1 H 0.226109 0.159238 0.595138 0.097 Uiso 1 1 calc R U . . .
C10 C 0.7744(9) 0.7640(4) 0.5896(4) 0.0558(15) Uani 1 1 d . . . . .
H9 H 0.910225 0.769956 0.566445 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7243(8) 0.6700(4) 0.6397(4) 0.0527(15) Uani 1 1 d . . . . .
H2 H 0.828757 0.612666 0.650648 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1400(9) 0.4785(5) 0.7590(4) 0.0529(15) Uani 1 1 d . . . . .
C13 C 0.5596(11) 0.3762(4) 0.6269(4) 0.0641(18) Uani 1 1 d . . . . .
H5 H 0.695550 0.403335 0.612125 0.077 Uiso 1 1 calc R U . . .
C14 C 0.4735(14) 0.2716(5) 0.5955(5) 0.080(2) Uani 1 1 d . . . . .
H6 H 0.553971 0.228432 0.558684 0.096 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(5) . ?
O1 C12 1.363(6) . ?
O1 C5 1.453(7) . ?
O2 C12 1.220(6) . ?
C1 C10 1.371(7) . ?
C1 C2 1.376(7) . ?
C2 C3 1.394(7) . ?
C2 H3 0.9300 . ?
C3 C4 1.375(6) . ?
C3 H4 0.9300 . ?
C4 C11 1.385(7) . ?
C4 C5 1.520(7) . ?
C5 C6 1.501(7) . ?
C5 H8 0.9800 . ?
C6 C13 1.378(8) . ?
C6 C7 1.382(7) . ?
C7 C8 1.392(8) . ?
C7 C12 1.449(8) . ?
C8 C9 1.367(9) . ?
C8 H7 0.9300 . ?
C9 C14 1.357(9) . ?
C9 H1 0.9300 . ?
C10 C11 1.383(7) . ?
C10 H9 0.9300 . ?
C11 H2 0.9300 . ?
C13 C14 1.390(9) . ?
C13 H5 0.9300 . ?
C14 H6 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
C12 O1 C5 109.8(4) . . ?
C10 C1 C2 121.4(5) . . ?
C10 C1 Br1 119.0(4) . . ?
C2 C1 Br1 119.6(4) . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H3 120.4 . . ?
C3 C2 H3 120.4 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H4 119.9 . . ?
C2 C3 H4 119.9 . . ?
C3 C4 C11 119.0(5) . . ?
C3 C4 C5 122.5(5) . . ?
C11 C4 C5 118.5(4) . . ?
O1 C5 C6 104.2(4) . . ?
O1 C5 C4 110.3(4) . . ?
C6 C5 C4 114.7(5) . . ?
O1 C5 H8 109.1 . . ?
C6 C5 H8 109.1 . . ?
C4 C5 H8 109.1 . . ?
C13 C6 C7 120.7(5) . . ?
C13 C6 C5 130.9(5) . . ?
C7 C6 C5 108.4(5) . . ?
C6 C7 C8 121.6(6) . . ?
C6 C7 C12 108.1(5) . . ?
C8 C7 C12 130.3(6) . . ?
C9 C8 C7 117.0(6) . . ?
C9 C8 H7 121.5 . . ?
C7 C8 H7 121.5 . . ?
C14 C9 C8 121.6(6) . . ?
C14 C9 H1 119.2 . . ?
C8 C9 H1 119.2 . . ?
C1 C10 C11 118.5(5) . . ?
C1 C10 H9 120.8 . . ?
C11 C10 H9 120.8 . . ?
C10 C11 C4 121.5(5) . . ?
C10 C11 H2 119.3 . . ?
C4 C11 H2 119.3 . . ?
O2 C12 O1 119.5(6) . . ?
O2 C12 C7 131.1(6) . . ?
O1 C12 C7 109.5(5) . . ?
C6 C13 C14 116.9(6) . . ?
C6 C13 H5 121.6 . . ?
C14 C13 H5 121.6 . . ?
C9 C14 C13 122.2(7) . . ?
C9 C14 H6 118.9 . . ?
C13 C14 H6 118.9 . . ?

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
C10 C1 C2 C3 -1.2(9) . . . . ?
Br1 C1 C2 C3 178.4(4) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C3 C4 C11 0.9(8) . . . . ?
C2 C3 C4 C5 -178.4(5) . . . . ?
C12 O1 C5 C6 1.4(5) . . . . ?
C12 O1 C5 C4 125.0(5) . . . . ?
C3 C4 C5 O1 -15.2(7) . . . . ?
C11 C4 C5 O1 165.5(5) . . . . ?
C3 C4 C5 C6 102.1(6) . . . . ?
C11 C4 C5 C6 -77.3(6) . . . . ?
O1 C5 C6 C13 179.3(6) . . . . ?
C4 C5 C6 C13 58.6(8) . . . . ?
O1 C5 C6 C7 -1.2(5) . . . . ?
C4 C5 C6 C7 -121.9(5) . . . . ?
C13 C6 C7 C8 -0.4(8) . . . . ?
C5 C6 C7 C8 -179.9(5) . . . . ?
C13 C6 C7 C12 -179.9(5) . . . . ?
C5 C6 C7 C12 0.5(6) . . . . ?
C6 C7 C8 C9 1.1(9) . . . . ?
C12 C7 C8 C9 -179.4(6) . . . . ?
C7 C8 C9 C14 -1.6(10) . . . . ?
C2 C1 C10 C11 0.6(8) . . . . ?
Br1 C1 C10 C11 -179.0(4) . . . . ?
C1 C10 C11 C4 0.7(8) . . . . ?
C3 C4 C11 C10 -1.5(9) . . . . ?
C5 C4 C11 C10 177.8(5) . . . . ?
C5 O1 C12 O2 180.0(5) . . . . ?
C5 O1 C12 C7 -1.1(6) . . . . ?
C6 C7 C12 O2 179.1(6) . . . . ?
C8 C7 C12 O2 -0.4(11) . . . . ?
C6 C7 C12 O1 0.4(6) . . . . ?
C8 C7 C12 O1 -179.1(5) . . . . ?
C7 C6 C13 C14 0.0(8) . . . . ?
C5 C6 C13 C14 179.4(6) . . . . ?
C8 C9 C14 C13 1.3(11) . . . . ?
C6 C13 C14 C9 -0.4(10) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.058



