# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_J457
_database_code_depnum_ccdc_archive 'CCDC 2025981'
loop_
_audit_author_name
_audit_author_address
'Tan Geok Kheng'
;National University of Singapore, Chemistry 
Singapore
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 Cl4 O10'
_chemical_formula_weight         744.41

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.5190(5)
_cell_length_b                   14.5588(7)
_cell_length_c                   22.7509(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3484.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9687
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.41

_exptl_crystal_description       Rod
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.396
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus Sealed Tube'
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68486
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4310
_reflns_number_gt                3809
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_bruker_data_scaling   'SADABS V2018/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.1722P)²+4.8478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual-space
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4310
_refine_ls_number_parameters     267
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2702
_refine_ls_wR_factor_gt          0.2590
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.081
_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
O1 O 0.23634(19) 0.75832(13) 0.35174(8) 0.0292(4) Uani 1 1 d D . . . .
H11 H 0.216(3) 0.719(2) 0.3257(13) 0.035 Uiso 1 1 d D U . . .
O2 O 0.3042(2) 0.57630(12) 0.35193(8) 0.0294(4) Uani 1 1 d D . . . .
H21 H 0.333(3) 0.5215(15) 0.3556(16) 0.035 Uiso 1 1 d D U . . .
O3 O 0.41478(18) 0.86050(18) 0.75115(8) 0.0392(6) Uani 1 1 d D . . . .
H31 H 0.357(3) 0.877(3) 0.7731(16) 0.047 Uiso 1 1 d D U . . .
O4 O 0.16181(18) 0.82890(15) 0.75015(8) 0.0314(5) Uani 1 1 d D . . . .
H41 H 0.0832(18) 0.831(3) 0.7496(18) 0.038 Uiso 1 1 d D U . . .
C1 C 0.6193(2) 1.02429(16) 0.47970(10) 0.0236(5) Uani 1 1 d . . . . .
H1 H 0.701562 1.040386 0.465836 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5964(2) 0.93512(16) 0.49922(10) 0.0223(5) Uani 1 1 d . . . . .
H2 H 0.663162 0.891196 0.498480 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4770(2) 0.90959(15) 0.51975(9) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.4550(2) 0.81100(15) 0.54034(9) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.539797 0.787119 0.553051 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4103(2) 0.74821(15) 0.49080(9) 0.0186(4) Uani 1 1 d . . . . .
C6 C 0.3402(2) 0.78064(15) 0.44332(9) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.316322 0.843545 0.441915 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3044(2) 0.72211(16) 0.39780(9) 0.0211(5) Uani 1 1 d . . . . .
C8 C 0.3402(2) 0.62964(16) 0.39901(10) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.4099(3) 0.59676(16) 0.44640(11) 0.0263(5) Uani 1 1 d . . . . .
H9 H 0.434197 0.533956 0.447728 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4442(2) 0.65569(16) 0.49209(10) 0.0233(5) Uani 1 1 d . . . . .
H10 H 0.491328 0.632460 0.524471 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3708(2) 0.80964(15) 0.59464(9) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.4273(2) 0.83211(18) 0.64850(10) 0.0241(5) Uani 1 1 d . . . . .
H12 H 0.516212 0.843121 0.650169 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3557(2) 0.83852(18) 0.69923(10) 0.0246(5) Uani 1 1 d . . . . .
C14 C 0.2249(2) 0.82219(18) 0.69766(10) 0.0239(5) Uani 1 1 d . . . . .
C15 C 0.1676(2) 0.80090(19) 0.64426(10) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.078425 0.790803 0.642572 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2405(2) 0.79431(18) 0.59306(10) 0.0243(5) Uani 1 1 d . . . . .
H16 H 0.200643 0.779204 0.556867 0.029 Uiso 1 1 calc R U . . .
C1S C 0.3179(8) 0.4337(5) 0.1567(3) 0.0525(14) Uani 0.673(7) 1 d . U P A 1
H1S1 H 0.291385 0.387199 0.127414 0.063 Uiso 0.673(7) 1 calc R U P A 1
H1S2 H 0.310449 0.494882 0.137935 0.063 Uiso 0.673(7) 1 calc R U P A 1
Cl1 Cl 0.2124(3) 0.42891(12) 0.21780(9) 0.0614(7) Uani 0.673(7) 1 d . U P A 1
Cl2 Cl 0.4741(3) 0.4150(2) 0.17471(15) 0.0842(8) Uani 0.673(7) 1 d . U P A 1
C1X C 0.377(2) 0.4333(15) 0.1662(10) 0.078(4) Uani 0.327(7) 1 d . U P A 2
H1X1 H 0.351616 0.381287 0.140679 0.094 Uiso 0.327(7) 1 calc R U P A 2
H1X2 H 0.345538 0.489861 0.146921 0.094 Uiso 0.327(7) 1 calc R U P A 2
Cl3 Cl 0.2961(9) 0.4221(4) 0.2292(2) 0.091(2) Uani 0.327(7) 1 d . U P A 2
Cl4 Cl 0.5355(11) 0.4381(7) 0.1648(4) 0.124(3) Uani 0.327(7) 1 d . U P A 2
O1W O 0.4152(3) 0.41190(16) 0.36177(13) 0.0443(7) Uani 0.901(6) 1 d D . P B 1
H1W H 0.480(4) 0.405(4) 0.339(2) 0.053 Uiso 0.901(6) 1 d D U P B 1
H2W H 0.368(4) 0.367(2) 0.353(2) 0.053 Uiso 0.901(6) 1 d D U P B 1
O2W O 0.523(3) 0.4166(16) 0.3399(13) 0.0443(7) Uani 0.099(6) 1 d . . P B 2


_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
O1 C7 1.374(3) . ?
O1 H11 0.857(18) . ?
O2 C8 1.376(3) . ?
O2 H21 0.858(18) . ?
O3 C13 1.372(3) . ?
O3 H31 0.825(19) . ?
O4 C14 1.370(3) . ?
O4 H41 0.828(19) . ?
C1 C2 1.393(3) . ?
C1 C3 1.398(3) 5_676 ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.527(3) . ?
C4 C11 1.520(3) . ?
C4 C5 1.525(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.391(3) . ?
C5 C10 1.394(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.389(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C1S Cl2 1.715(8) . ?
C1S Cl1 1.781(7) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C1X Cl4 1.67(2) . ?
C1X Cl3 1.68(2) . ?
C1X H1X1 0.9900 . ?
C1X H1X2 0.9900 . ?
O1W H1W 0.86(2) . ?
O1W H2W 0.842(19) . ?

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
C7 O1 H11 114(3) . . ?
C8 O2 H21 111(3) . . ?
C13 O3 H31 105(3) . . ?
C14 O4 H41 118(3) . . ?
C2 C1 C3 120.9(2) . 5_676 ?
C2 C1 H1 119.6 . . ?
C3 C1 H1 119.6 5_676 . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C1 118.3(2) . 5_676 ?
C2 C3 C4 119.43(19) . . ?
C1 C3 C4 122.29(19) 5_676 . ?
C11 C4 C5 114.39(18) . . ?
C11 C4 C3 110.48(17) . . ?
C5 C4 C3 112.54(17) . . ?
C11 C4 H4 106.3 . . ?
C5 C4 H4 106.3 . . ?
C3 C4 H4 106.3 . . ?
C6 C5 C10 118.7(2) . . ?
C6 C5 C4 122.27(19) . . ?
C10 C5 C4 119.00(19) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
O1 C7 C6 118.2(2) . . ?
O1 C7 C8 121.7(2) . . ?
C6 C7 C8 120.1(2) . . ?
O2 C8 C9 123.7(2) . . ?
O2 C8 C7 117.0(2) . . ?
C9 C8 C7 119.3(2) . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.8(2) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C16 C11 C12 118.6(2) . . ?
C16 C11 C4 123.78(19) . . ?
C12 C11 C4 117.43(19) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O3 C13 C12 119.2(2) . . ?
O3 C13 C14 120.5(2) . . ?
C12 C13 C14 120.3(2) . . ?
O4 C14 C15 124.6(2) . . ?
O4 C14 C13 116.3(2) . . ?
C15 C14 C13 119.2(2) . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
Cl2 C1S Cl1 113.8(4) . . ?
Cl2 C1S H1S1 108.8 . . ?
Cl1 C1S H1S1 108.8 . . ?
Cl2 C1S H1S2 108.8 . . ?
Cl1 C1S H1S2 108.8 . . ?
H1S1 C1S H1S2 107.7 . . ?
Cl4 C1X Cl3 121.8(13) . . ?
Cl4 C1X H1X1 106.9 . . ?
Cl3 C1X H1X1 106.9 . . ?
Cl4 C1X H1X2 106.9 . . ?
Cl3 C1X H1X2 106.9 . . ?
H1X1 C1X H1X2 106.7 . . ?
H1W O1W H2W 103(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
C3 C1 C2 C3 0.0(4) 5_676 . . . ?
C1 C2 C3 C1 0.0(4) . . . 5_676 ?
C1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C11 140.6(2) . . . . ?
C1 C3 C4 C11 -39.9(3) 5_676 . . . ?
C2 C3 C4 C5 -90.1(2) . . . . ?
C1 C3 C4 C5 89.3(2) 5_676 . . . ?
C11 C4 C5 C6 97.9(2) . . . . ?
C3 C4 C5 C6 -29.3(3) . . . . ?
C11 C4 C5 C10 -84.2(2) . . . . ?
C3 C4 C5 C10 148.7(2) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 177.9(2) . . . . ?
C5 C6 C7 O1 -179.3(2) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
O1 C7 C8 O2 0.0(3) . . . . ?
C6 C7 C8 O2 -178.5(2) . . . . ?
O1 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
O2 C8 C9 C10 179.1(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C6 C5 C10 C9 0.7(3) . . . . ?
C4 C5 C10 C9 -177.3(2) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C5 C4 C11 C16 -31.0(3) . . . . ?
C3 C4 C11 C16 97.2(3) . . . . ?
C5 C4 C11 C12 154.1(2) . . . . ?
C3 C4 C11 C12 -77.7(2) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C4 C11 C12 C13 175.6(2) . . . . ?
C11 C12 C13 O3 179.8(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
O3 C13 C14 O4 -0.4(4) . . . . ?
C12 C13 C14 O4 179.2(2) . . . . ?
O3 C13 C14 C15 179.4(2) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
O4 C14 C15 C16 -179.1(2) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C4 C11 C16 C15 -175.1(2) . . . . ?
C14 C15 C16 C11 -0.6(4) . . . . ?

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
_geom_hbond_publ_flag
O1 H11 O4 0.857(18) 1.94(2) 2.751(2) 158(4) 7_575 yes
O2 H21 O1W^a 0.858(18) 1.820(19) 2.672(3) 172(4) . yes
O2 H21 O2W^b 0.858(18) 2.54(4) 3.28(3) 146(3) . yes
O3 H31 O2 0.825(19) 1.99(3) 2.731(3) 148(4) 7_576 yes
O3 H31 O4 0.825(19) 2.23(4) 2.700(3) 116(4) . yes
O4 H41 O3 0.828(19) 1.82(2) 2.639(3) 168(4) 6_557 yes
C9 H9 O1W^a 0.95 2.65 3.310(4) 127.0 . yes
O1W^a H1W^a Cl1^a 0.86(2) 2.79(3) 3.622(4) 163(5) 6_656 yes
O1W^a H2W^a O1 0.842(19) 1.93(2) 2.755(3) 167(5) 8_655 yes

_refine_diff_density_max         0.903
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.125

