# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_p21_b
_database_code_depnum_ccdc_archive 'CCDC 2246696'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Imagawa'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(2S,3R,6R,7R,E)-7-((4-bromobenzoyl)oxy)-6-methoxy-7-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-4-ene-2,3-diyl diacetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Br O9'
_chemical_formula_weight         539.36

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   13.5903(13)
_cell_length_b                   6.6575(6)
_cell_length_c                   13.8833(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.1930(10)
_cell_angle_gamma                90
_cell_volume                     1236.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7428
_cell_measurement_theta_min      1.490
_cell_measurement_theta_max      29.194

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.712
_shelx_estimated_absorpt_T_min   0.426
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            7428
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         29.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_point_group_measured_fraction_full 0.852
_reflns_number_total             4996
_reflns_number_gt                4579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.505
_reflns_Friedel_fraction_max     0.547
_reflns_Friedel_fraction_full    0.675

_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       'ApexII (Bruker AXS Inc.'
_computing_cell_refinement       'ApexII (Bruker AXS Inc.'
_computing_data_reduction        'ApexII (Bruker AXS Inc.'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ApexII (Bruker AXS Inc.'
_computing_publication_material  'ApexII (Bruker AXS Inc.'
_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)] 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 1434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4996
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
Br01 Br 0.02168(2) 0.03719(4) 1.18134(2) 0.03002(8) Uani 1 1 d . . . . .
O002 O 0.35281(11) 0.6121(2) 0.40602(13) 0.0220(4) Uani 1 1 d . . . . .
O003 O 0.15379(11) 0.7782(3) 0.37999(12) 0.0198(3) Uani 1 1 d . . . . .
O004 O 0.27181(12) 0.3061(2) 0.82121(12) 0.0219(4) Uani 1 1 d . . . . .
O005 O 0.47272(12) 0.2316(3) 0.82095(12) 0.0254(4) Uani 1 1 d . . . . .
O006 O 0.24556(14) -0.0185(3) 0.77731(15) 0.0301(4) Uani 1 1 d . . . . .
O007 O 0.15805(13) 0.4122(3) 0.64672(13) 0.0268(4) Uani 1 1 d . . . . .
O008 O 0.61050(14) 0.0978(3) 0.90383(15) 0.0361(5) Uani 1 1 d . . . . .
O009 O 0.51581(13) 0.6888(3) 0.42883(16) 0.0343(5) Uani 1 1 d . . . . .
O00A O 0.17427(14) 0.6262(3) 0.23909(15) 0.0336(5) Uani 1 1 d . . . . .
C7 C 0.23915(17) 0.1177(4) 0.83221(19) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.10311(19) -0.1034(4) 1.0195(2) 0.0240(5) Uani 1 1 d . . . . .
H00C H 0.0747 -0.2255 1.0322 0.029 Uiso 1 1 calc R U . . .
C14 C 0.25499(17) 0.5039(4) 0.67560(18) 0.0225(5) Uani 1 1 d . . . . .
H00D H 0.2497 0.6250 0.7145 0.027 Uiso 1 1 calc R U . . .
C15 C 0.29672(15) 0.5549(4) 0.58518(16) 0.0198(4) Uani 1 1 d . . . . .
H00E H 0.3212 0.4509 0.5514 0.024 Uiso 1 1 calc R U . . .
C4 C 0.19261(17) 0.1028(4) 0.92172(19) 0.0203(5) Uani 1 1 d . . . . .
C9 C 0.42445(18) 0.4109(4) 0.77461(18) 0.0208(5) Uani 1 1 d . . . . .
H00G H 0.4558 0.4453 0.7184 0.025 Uiso 1 1 calc R U . . .
C21 C 0.44811(16) 0.5814(4) 0.39444(17) 0.0209(5) Uani 1 1 d . . . . .
C8 C 0.31788(18) 0.3459(4) 0.73711(18) 0.0212(5) Uani 1 1 d . . . . .
H00I H 0.3182 0.2225 0.6987 0.025 Uiso 1 1 calc R U . . .
C5 C 0.18982(18) 0.2633(4) 0.98540(19) 0.0229(5) Uani 1 1 d . . . . .
H00J H 0.2198 0.3846 0.9742 0.027 Uiso 1 1 calc R U . . .
C3 C 0.15138(18) -0.0820(4) 0.94007(19) 0.0226(5) Uani 1 1 d . . . . .
H00K H 0.1562 -0.1908 0.8991 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5668(2) 0.2485(4) 0.8729(2) 0.0272(6) Uani 1 1 d . . . . .
C6 C 0.14254(19) 0.2431(4) 1.0653(2) 0.0257(5) Uani 1 1 d . . . . .
H00M H 0.1406 0.3494 1.1084 0.031 Uiso 1 1 calc R U . . .
C16 C 0.30039(16) 0.7401(4) 0.55112(18) 0.0204(5) Uani 1 1 d . . . . .
H00N H 0.2840 0.8448 0.5897 0.024 Uiso 1 1 calc R U . . .
C1 C 0.09821(16) 0.0612(5) 1.07965(17) 0.0239(5) Uani 1 1 d . . . . .
C18 C 0.24459(18) 0.8955(4) 0.38496(19) 0.0197(5) Uani 1 1 d . . . . .
H1A H 0.2624 0.9026 0.3196 0.024 Uiso 1 1 calc R U . . .
C23 C 0.12714(19) 0.6509(4) 0.30344(19) 0.0247(5) Uani 1 1 d . . . . .
C10 C 0.43764(18) 0.5859(3) 0.84520(19) 0.0253(6) Uani 1 1 d . . . . .
H00A H 0.4120 0.7078 0.8116 0.030 Uiso 1 1 calc R U . . .
H00B H 0.4009 0.5614 0.8979 0.030 Uiso 1 1 calc R U . . .
C17 C 0.32908(17) 0.7928(4) 0.45485(18) 0.0202(5) Uani 1 1 d . . . . .
H00S H 0.3877 0.8810 0.4661 0.024 Uiso 1 1 calc R U . . .
C24 C 0.02988(16) 0.5517(5) 0.31048(19) 0.0324(6) Uani 1 1 d . . . . .
H00F H 0.0058 0.4800 0.2510 0.049 Uiso 1 1 calc R U . . .
H00H H -0.0181 0.6519 0.3205 0.049 Uiso 1 1 calc R U . . .
H00L H 0.0395 0.4595 0.3645 0.049 Uiso 1 1 calc R U . . .
C22 C 0.4558(2) 0.3950(4) 0.3364(2) 0.0283(6) Uani 1 1 d . . . . .
H00O H 0.5171 0.3971 0.3111 0.042 Uiso 1 1 calc R U . . .
H00Q H 0.4002 0.3885 0.2831 0.042 Uiso 1 1 calc R U . . .
H00R H 0.4549 0.2796 0.3777 0.042 Uiso 1 1 calc R U . . .
C19 C 0.22215(19) 1.1047(4) 0.4176(2) 0.0267(6) Uani 1 1 d . . . . .
H00T H 0.1707 1.1641 0.3699 0.040 Uiso 1 1 calc R U . . .
H00U H 0.2815 1.1854 0.4243 0.040 Uiso 1 1 calc R U . . .
H00V H 0.2000 1.0974 0.4795 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6071(2) 0.4525(4) 0.8928(2) 0.0351(7) Uani 1 1 d . . . . .
H00W H 0.6758 0.4714 0.9105 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5464(2) 0.6092(4) 0.8857(2) 0.0333(7) Uani 1 1 d . . . . .
H00X H 0.5716 0.7350 0.9061 0.040 Uiso 1 1 calc R U . . .
C20 C 0.08455(17) 0.5529(6) 0.6052(2) 0.0361(6) Uani 1 1 d . . . . .
H00$ H 0.0843 0.6642 0.6492 0.054 Uiso 1 1 calc R U . . .
H00 H 0.0200 0.4897 0.5942 0.054 Uiso 1 1 calc R U . . .
H1 H 0.0995 0.6004 0.5441 0.054 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
Br01 C1 1.903(2) . ?
O002 C21 1.349(3) . ?
O002 C17 1.445(3) . ?
O003 C23 1.357(3) . ?
O003 C18 1.452(3) . ?
O004 C7 1.348(3) . ?
O004 C8 1.444(3) . ?
O005 C13 1.357(3) . ?
O005 C9 1.456(3) . ?
O006 C7 1.198(3) . ?
O007 C20 1.416(3) . ?
O007 C14 1.443(3) . ?
O008 C13 1.206(3) . ?
O009 C21 1.196(3) . ?
O00A C23 1.199(3) . ?
C7 C4 1.494(4) . ?
C2 C1 1.386(4) . ?
C2 C3 1.387(4) . ?
C2 H00C 0.9300 . ?
C14 C15 1.505(3) . ?
C14 C8 1.519(3) . ?
C14 H00D 0.9800 . ?
C15 C16 1.324(4) . ?
C15 H00E 0.9300 . ?
C4 C5 1.392(4) . ?
C4 C3 1.394(3) . ?
C9 C10 1.512(3) . ?
C9 C8 1.513(3) . ?
C9 H00G 0.9800 . ?
C21 C22 1.493(4) . ?
C8 H00I 0.9800 . ?
C5 C6 1.383(4) . ?
C5 H00J 0.9300 . ?
C3 H00K 0.9300 . ?
C13 C12 1.473(4) . ?
C6 C1 1.383(4) . ?
C6 H00M 0.9300 . ?
C16 C17 1.499(4) . ?
C16 H00N 0.9300 . ?
C18 C19 1.513(3) . ?
C18 C17 1.527(3) . ?
C18 H1A 0.9800 . ?
C23 C24 1.496(4) . ?
C10 C11 1.493(4) . ?
C10 H00A 0.9700 . ?
C10 H00B 0.9700 . ?
C17 H00S 0.9800 . ?
C24 H00F 0.9600 . ?
C24 H00H 0.9600 . ?
C24 H00L 0.9600 . ?
C22 H00O 0.9600 . ?
C22 H00Q 0.9600 . ?
C22 H00R 0.9600 . ?
C19 H00T 0.9600 . ?
C19 H00U 0.9600 . ?
C19 H00V 0.9600 . ?
C12 C11 1.323(4) . ?
C12 H00W 0.9300 . ?
C11 H00X 0.9300 . ?
C20 H00$ 0.9600 . ?
C20 H00 0.9600 . ?
C20 H1 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
C21 O002 C17 118.75(19) . . ?
C23 O003 C18 118.67(19) . . ?
C7 O004 C8 117.44(19) . . ?
C13 O005 C9 118.40(19) . . ?
C20 O007 C14 112.1(2) . . ?
O006 C7 O004 124.7(2) . . ?
O006 C7 C4 124.6(2) . . ?
O004 C7 C4 110.6(2) . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H00C 120.7 . . ?
C3 C2 H00C 120.7 . . ?
O007 C14 C15 108.91(19) . . ?
O007 C14 C8 104.98(19) . . ?
C15 C14 C8 111.6(2) . . ?
O007 C14 H00D 110.4 . . ?
C15 C14 H00D 110.4 . . ?
C8 C14 H00D 110.4 . . ?
C16 C15 C14 123.5(2) . . ?
C16 C15 H00E 118.3 . . ?
C14 C15 H00E 118.3 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 C7 122.7(2) . . ?
C3 C4 C7 117.0(2) . . ?
O005 C9 C10 110.6(2) . . ?
O005 C9 C8 104.27(18) . . ?
C10 C9 C8 116.1(2) . . ?
O005 C9 H00G 108.5 . . ?
C10 C9 H00G 108.5 . . ?
C8 C9 H00G 108.5 . . ?
O009 C21 O002 123.3(2) . . ?
O009 C21 C22 126.2(2) . . ?
O002 C21 C22 110.5(2) . . ?
O004 C8 C9 107.45(19) . . ?
O004 C8 C14 107.47(19) . . ?
C9 C8 C14 113.9(2) . . ?
O004 C8 H00I 109.3 . . ?
C9 C8 H00I 109.3 . . ?
C14 C8 H00I 109.3 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H00J 119.9 . . ?
C4 C5 H00J 119.9 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H00K 120.1 . . ?
C4 C3 H00K 120.1 . . ?
O008 C13 O005 118.6(2) . . ?
O008 C13 C12 123.9(2) . . ?
O005 C13 C12 117.4(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H00M 120.8 . . ?
C5 C6 H00M 120.8 . . ?
C15 C16 C17 124.7(2) . . ?
C15 C16 H00N 117.7 . . ?
C17 C16 H00N 117.7 . . ?
C6 C1 C2 122.5(2) . . ?
C6 C1 Br01 119.3(2) . . ?
C2 C1 Br01 118.1(2) . . ?
O003 C18 C19 107.14(18) . . ?
O003 C18 C17 109.05(19) . . ?
C19 C18 C17 113.0(2) . . ?
O003 C18 H1A 109.2 . . ?
C19 C18 H1A 109.2 . . ?
C17 C18 H1A 109.2 . . ?
O00A C23 O003 124.4(2) . . ?
O00A C23 C24 125.6(2) . . ?
O003 C23 C24 109.9(2) . . ?
C11 C10 C9 108.7(2) . . ?
C11 C10 H00A 110.0 . . ?
C9 C10 H00A 110.0 . . ?
C11 C10 H00B 110.0 . . ?
C9 C10 H00B 110.0 . . ?
H00A C10 H00B 108.3 . . ?
O002 C17 C16 109.8(2) . . ?
O002 C17 C18 106.25(19) . . ?
C16 C17 C18 112.73(19) . . ?
O002 C17 H00S 109.3 . . ?
C16 C17 H00S 109.3 . . ?
C18 C17 H00S 109.3 . . ?
C23 C24 H00F 109.5 . . ?
C23 C24 H00H 109.5 . . ?
H00F C24 H00H 109.5 . . ?
C23 C24 H00L 109.5 . . ?
H00F C24 H00L 109.5 . . ?
H00H C24 H00L 109.5 . . ?
C21 C22 H00O 109.5 . . ?
C21 C22 H00Q 109.5 . . ?
H00O C22 H00Q 109.5 . . ?
C21 C22 H00R 109.5 . . ?
H00O C22 H00R 109.5 . . ?
H00Q C22 H00R 109.5 . . ?
C18 C19 H00T 109.5 . . ?
C18 C19 H00U 109.5 . . ?
H00T C19 H00U 109.5 . . ?
C18 C19 H00V 109.5 . . ?
H00T C19 H00V 109.5 . . ?
H00U C19 H00V 109.5 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H00W 119.8 . . ?
C13 C12 H00W 119.8 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H00X 119.7 . . ?
C10 C11 H00X 119.7 . . ?
O007 C20 H00$ 109.5 . . ?
O007 C20 H00 109.5 . . ?
H00$ C20 H00 109.5 . . ?
O007 C20 H1 109.5 . . ?
H00$ C20 H1 109.5 . . ?
H00 C20 H1 109.5 . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.050



