# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1985212'
loop_
_audit_author_name
_audit_author_address
'Sunil Varughese'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-07-15 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            'C23 H21 Cl O7'
_chemical_formula_weight         444.85

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   9.040(9)
_cell_length_b                   16.150(8)
_cell_length_c                   14.320(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.670(6)
_cell_angle_gamma                90
_cell_volume                     2047(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_process_details   
;
Jacobson method
;
_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  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7855
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1841
_reflns_number_gt                1332
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2018/3 (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)+(0.0608P)²+3.4948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1841
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.1275
_refine_ls_wR_factor_ref         0.2347
_refine_ls_wR_factor_gt          0.2138
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_restrained_S_all      1.328
_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
Cl1 Cl 0.750000 0.30804(13) 0.000000 0.0716(8) Uani 1 2 d S T P . .
O1 O 0.6812(7) 0.3576(3) 0.0582(4) 0.147(3) Uani 1 1 d . . . . .
O12 O 0.8600(6) 0.2587(3) 0.0567(4) 0.124(2) Uani 1 1 d . . . . .
O22 O 0.7518(4) -0.1178(2) 0.3219(3) 0.0793(13) Uani 1 1 d . . . . .
O27 O 0.250000 0.0370(2) 0.000000 0.0504(13) Uani 1 2 d S T P . .
C2 C 0.5934(9) 0.1579(4) 0.1889(5) 0.090(2) Uani 1 1 d . . . . .
H2A H 0.632408 0.178012 0.253023 0.108 Uiso 1 1 calc R U . . .
H2B H 0.668516 0.169875 0.151104 0.108 Uiso 1 1 calc R U . . .
C7 C 0.8649(7) -0.0799(4) 0.3948(5) 0.087(2) Uani 1 1 d . . . . .
H7A H 0.918868 -0.122081 0.435095 0.131 Uiso 1 1 calc R U . . .
H7B H 0.816975 -0.043221 0.432395 0.131 Uiso 1 1 calc R U . . .
H7C H 0.934195 -0.049041 0.365573 0.131 Uiso 1 1 calc R U . . .
C8 C 0.5746(7) 0.0648(3) 0.1932(4) 0.0599(15) Uani 1 1 d . . . . .
C9 C 0.4581(9) 0.2035(4) 0.1497(6) 0.104(3) Uani 1 1 d . . . . .
H9A H 0.487149 0.256946 0.128260 0.125 Uiso 1 1 calc R U . . .
H9B H 0.403335 0.213507 0.200283 0.125 Uiso 1 1 calc R U . . .
C11 C 0.6608(6) -0.0677(3) 0.2586(4) 0.0592(15) Uani 1 1 d . . . . .
C14 C 0.6737(7) 0.0184(3) 0.2589(4) 0.0612(15) Uani 1 1 d . . . . .
H14 H 0.748802 0.044383 0.303160 0.073 Uiso 1 1 calc R U . . .
C16 C 0.250000 0.2041(5) 0.000000 0.082(3) Uani 1 2 d S T P . .
H16 H 0.250000 0.261530 0.000000 0.098 Uiso 1 2 d R U P . .
C17 C 0.4526(6) -0.0612(3) 0.1262(4) 0.0545(15) Uani 1 1 d . . . . .
H17 H 0.380252 -0.087651 0.080451 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4607(6) 0.0259(3) 0.1281(4) 0.0505(14) Uani 1 1 d . . . . .
C24 C 0.3531(7) 0.1625(3) 0.0683(4) 0.0652(17) Uani 1 1 d . . . . .
C25 C 0.3548(6) 0.0770(3) 0.0644(4) 0.0487(13) Uani 1 1 d . . . . .
C40 C 0.5511(6) -0.1073(3) 0.1916(4) 0.0596(15) Uani 1 1 d . . . . .
H40 H 0.544289 -0.164738 0.191010 0.072 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
Cl1 O1 1.390(5) 2_655 ?
Cl1 O1 1.390(5) . ?
Cl1 O12 1.398(4) . ?
Cl1 O12 1.398(4) 2_655 ?
O22 C11 1.360(6) . ?
O22 C7 1.442(6) . ?
O27 C25 1.346(5) . ?
O27 C25 1.346(5) 2 ?
C2 C9 1.440(9) . ?
C2 C8 1.516(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C14 1.383(7) . ?
C8 C18 1.391(7) . ?
C9 C24 1.501(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C40 1.388(7) . ?
C11 C14 1.395(7) . ?
C14 H14 0.9300 . ?
C16 C24 1.380(7) 2 ?
C16 C24 1.380(7) . ?
C16 H16 0.9278 . ?
C17 C40 1.373(7) . ?
C17 C18 1.410(6) . ?
C17 H17 0.9300 . ?
C18 C25 1.441(7) . ?
C24 C25 1.382(7) . ?
C40 H40 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
O1 Cl1 O1 109.7(6) 2_655 . ?
O1 Cl1 O12 108.9(3) 2_655 . ?
O1 Cl1 O12 109.4(3) . . ?
O1 Cl1 O12 109.4(3) 2_655 2_655 ?
O1 Cl1 O12 108.9(3) . 2_655 ?
O12 Cl1 O12 110.5(5) . 2_655 ?
C11 O22 C7 118.4(5) . . ?
C25 O27 C25 122.6(5) . 2 ?
C9 C2 C8 115.4(6) . . ?
C9 C2 H2A 108.4 . . ?
C8 C2 H2A 108.4 . . ?
C9 C2 H2B 108.4 . . ?
C8 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
O22 C7 H7A 109.5 . . ?
O22 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O22 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C8 C18 120.1(5) . . ?
C14 C8 C2 120.2(5) . . ?
C18 C8 C2 119.7(5) . . ?
C2 C9 C24 115.6(5) . . ?
C2 C9 H9A 108.4 . . ?
C24 C9 H9A 108.4 . . ?
C2 C9 H9B 108.4 . . ?
C24 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
O22 C11 C40 116.0(5) . . ?
O22 C11 C14 123.4(5) . . ?
C40 C11 C14 120.5(5) . . ?
C8 C14 C11 119.8(5) . . ?
C8 C14 H14 120.1 . . ?
C11 C14 H14 120.1 . . ?
C24 C16 C24 121.8(7) 2 . ?
C24 C16 H16 119.1 2 . ?
C24 C16 H16 119.1 . . ?
C40 C17 C18 120.2(5) . . ?
C40 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C8 C18 C17 119.5(5) . . ?
C8 C18 C25 118.2(5) . . ?
C17 C18 C25 122.3(5) . . ?
C16 C24 C25 118.0(6) . . ?
C16 C24 C9 124.5(5) . . ?
C25 C24 C9 117.5(5) . . ?
O27 C25 C24 119.7(5) . . ?
O27 C25 C18 116.4(4) . . ?
C24 C25 C18 123.9(5) . . ?
C17 C40 C11 119.8(5) . . ?
C17 C40 H40 120.1 . . ?
C11 C40 H40 120.1 . . ?

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
C9 C2 C8 C14 -155.3(7) . . . . ?
C9 C2 C8 C18 27.2(9) . . . . ?
C8 C2 C9 C24 -37.1(10) . . . . ?
C7 O22 C11 C40 -178.2(5) . . . . ?
C7 O22 C11 C14 1.9(8) . . . . ?
C18 C8 C14 C11 1.1(9) . . . . ?
C2 C8 C14 C11 -176.4(6) . . . . ?
O22 C11 C14 C8 -178.8(6) . . . . ?
C40 C11 C14 C8 1.3(9) . . . . ?
C14 C8 C18 C17 -3.6(8) . . . . ?
C2 C8 C18 C17 173.9(6) . . . . ?
C14 C8 C18 C25 176.6(5) . . . . ?
C2 C8 C18 C25 -5.9(8) . . . . ?
C40 C17 C18 C8 3.7(8) . . . . ?
C40 C17 C18 C25 -176.5(5) . . . . ?
C24 C16 C24 C25 2.5(4) 2 . . . ?
C24 C16 C24 C9 -174.0(7) 2 . . . ?
C2 C9 C24 C16 -155.8(6) . . . . ?
C2 C9 C24 C25 27.6(9) . . . . ?
C25 O27 C25 C24 2.6(4) 2 . . . ?
C25 O27 C25 C18 -179.3(5) 2 . . . ?
C16 C24 C25 O27 -5.1(7) . . . . ?
C9 C24 C25 O27 171.7(5) . . . . ?
C16 C24 C25 C18 177.0(4) . . . . ?
C9 C24 C25 C18 -6.2(9) . . . . ?
C8 C18 C25 O27 177.4(4) . . . . ?
C17 C18 C25 O27 -2.4(7) . . . . ?
C8 C18 C25 C24 -4.6(8) . . . . ?
C17 C18 C25 C24 175.6(5) . . . . ?
C18 C17 C40 C11 -1.2(9) . . . . ?
O22 C11 C40 C17 178.8(5) . . . . ?
C14 C11 C40 C17 -1.3(9) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044

