# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_Marek167b
_audit_block_doi                 10.5517/ccdc.csd.cc27mc8j
_database_code_depnum_ccdc_archive 'CCDC 2074187'
loop_
_audit_author_name
_audit_author_address
'Natalia Fridman'
;Technion
Israel
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Marek167b (Rahul Suresh)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_weight         292.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   18.000(3)
_cell_length_b                   5.5870(9)
_cell_length_c                   15.124(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.465(4)
_cell_angle_gamma                90
_cell_volume                     1516.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2499
_cell_measurement_theta_min      2.270
_cell_measurement_theta_max      24.552

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            9217
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         24.552
_diffrn_reflns_theta_full        24.552
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2499
_reflns_number_gt                1512
_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         2499
_refine_ls_number_parameters     196
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      0.985
_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 0.62305(10) 0.2287(3) 0.62707(12) 0.0436(5) Uani 1 1 d . U . . .
O2 O 0.74883(10) 0.5506(4) 0.73886(12) 0.0523(6) Uani 1 1 d . U . . .
O3 O 0.80376(10) 0.2425(3) 0.67455(11) 0.0471(5) Uani 1 1 d . U . . .
O4 O 0.96145(13) 0.7391(4) 0.45025(16) 0.0749(7) Uani 1 1 d D U . . .
H4 H 0.9976(15) 0.862(4) 0.443(3) 0.155(19) Uiso 1 1 d D . . . .
O5 O 0.93797(12) 0.9331(5) 0.57195(16) 0.0792(8) Uani 1 1 d . U . . .
C1 C 0.52552(13) 0.5130(4) 0.62416(14) 0.0279(6) Uani 1 1 d . U . . .
C2 C 0.47940(14) 0.3605(5) 0.66790(15) 0.0335(6) Uani 1 1 d . U . . .
H2 H 0.4980 0.2101 0.6889 0.040 Uiso 1 1 calc R U . . .
C3 C 0.40692(14) 0.4250(5) 0.68116(16) 0.0394(7) Uani 1 1 d . U . . .
H3 H 0.3760 0.3209 0.7118 0.047 Uiso 1 1 calc R U . . .
C4 C 0.37998(15) 0.6428(5) 0.64925(17) 0.0428(7) Uani 1 1 d . U . . .
H4A H 0.3302 0.6882 0.6579 0.051 Uiso 1 1 calc R U . . .
C5 C 0.42447(14) 0.7937(5) 0.60519(17) 0.0408(7) Uani 1 1 d . U . . .
H5 H 0.4052 0.9422 0.5831 0.049 Uiso 1 1 calc R U . . .
C6 C 0.49729(14) 0.7310(4) 0.59274(16) 0.0346(7) Uani 1 1 d . U . . .
H6 H 0.5280 0.8372 0.5627 0.042 Uiso 1 1 calc R U . . .
C7 C 0.60366(13) 0.4347(5) 0.61170(15) 0.0307(6) Uani 1 1 d . U . . .
C8 C 0.65730(12) 0.6149(4) 0.57919(16) 0.0316(6) Uani 1 1 d . U . . .
H8A H 0.6573 0.7593 0.6171 0.038 Uiso 1 1 calc R U . . .
H8B H 0.6401 0.6632 0.5180 0.038 Uiso 1 1 calc R U . . .
C9 C 0.73644(13) 0.5188(4) 0.57988(15) 0.0320(6) Uani 1 1 d . U . . .
H9 H 0.7363 0.3759 0.5401 0.038 Uiso 1 1 calc R U . . .
C10 C 0.76215(14) 0.4415(5) 0.67319(18) 0.0358(7) Uani 1 1 d . U . . .
C11 C 0.83532(17) 0.1568(6) 0.76019(19) 0.0625(9) Uani 1 1 d . U . . .
H11A H 0.8031 0.2065 0.8070 0.075 Uiso 1 1 calc R U . . .
H11B H 0.8374 -0.0203 0.7597 0.075 Uiso 1 1 calc R U . . .
C12 C 0.90977(19) 0.2523(8) 0.7798(2) 0.1052(16) Uani 1 1 d . U . . .
H12A H 0.9395 0.2237 0.7292 0.158 Uiso 1 1 calc R U . . .
H12B H 0.9333 0.1730 0.8325 0.158 Uiso 1 1 calc R U . . .
H12C H 0.9067 0.4248 0.7907 0.158 Uiso 1 1 calc R U . . .
C13 C 0.79198(13) 0.7043(5) 0.54808(16) 0.0348(7) Uani 1 1 d . U . . .
H13 H 0.7998 0.8302 0.5949 0.042 Uiso 1 1 calc R U . . .
C14 C 0.76450(16) 0.8266(6) 0.46165(19) 0.0579(9) Uani 1 1 d . U . . .
H14A H 0.7511 0.7050 0.4165 0.087 Uiso 1 1 calc R U . . .
H14B H 0.8041 0.9289 0.4415 0.087 Uiso 1 1 calc R U . . .
H14C H 0.7207 0.9245 0.4713 0.087 Uiso 1 1 calc R U . . .
C15 C 0.86736(14) 0.5860(5) 0.5362(2) 0.0541(8) Uani 1 1 d . U . . .
H15A H 0.8836 0.4955 0.5905 0.065 Uiso 1 1 calc R U . . .
H15B H 0.8616 0.4709 0.4863 0.065 Uiso 1 1 calc R U . . .
C16 C 0.92537(16) 0.7638(6) 0.5181(2) 0.0495(8) Uani 1 1 d . 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
O1 C7 1.220(3) . ?
O2 C10 1.205(3) . ?
O3 C10 1.339(3) . ?
O3 C11 1.455(3) . ?
O4 C16 1.264(3) . ?
O4 H4 0.9601(11) . ?
O5 C16 1.257(4) . ?
C1 C6 1.390(3) . ?
C1 C2 1.392(3) . ?
C1 C7 1.499(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.504(3) . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(3) . ?
C9 C13 1.543(3) . ?
C9 H9 1.0000 . ?
C11 C12 1.452(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.523(3) . ?
C13 C15 1.533(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.482(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C10 O3 C11 117.8(2) . . ?
C16 O4 H4 115(2) . . ?
C6 C1 C2 118.9(2) . . ?
C6 C1 C7 122.3(2) . . ?
C2 C1 C7 118.8(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C1 120.6(2) . . ?
O1 C7 C8 120.8(2) . . ?
C1 C7 C8 118.6(2) . . ?
C7 C8 C9 112.7(2) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 109.0(2) . . ?
C10 C9 C13 108.91(19) . . ?
C8 C9 C13 113.0(2) . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C13 C9 H9 108.6 . . ?
O2 C10 O3 123.6(2) . . ?
O2 C10 C9 123.9(3) . . ?
O3 C10 C9 112.4(2) . . ?
C12 C11 O3 110.5(3) . . ?
C12 C11 H11A 109.5 . . ?
O3 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 108.9(2) . . ?
C14 C13 C9 113.2(2) . . ?
C15 C13 C9 110.4(2) . . ?
C14 C13 H13 108.1 . . ?
C15 C13 H13 108.1 . . ?
C9 C13 H13 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 112.1(2) . . ?
C16 C15 H15A 109.2 . . ?
C13 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O5 C16 O4 122.0(3) . . ?
O5 C16 C15 118.7(3) . . ?
O4 C16 C15 119.3(3) . . ?

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
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C1 C2 C3 179.9(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?
C6 C1 C7 O1 -168.2(2) . . . . ?
C2 C1 C7 O1 11.1(3) . . . . ?
C6 C1 C7 C8 11.3(3) . . . . ?
C2 C1 C7 C8 -169.4(2) . . . . ?
O1 C7 C8 C9 -7.1(3) . . . . ?
C1 C7 C8 C9 173.36(19) . . . . ?
C7 C8 C9 C10 -57.9(3) . . . . ?
C7 C8 C9 C13 -179.04(19) . . . . ?
C11 O3 C10 O2 -1.0(4) . . . . ?
C11 O3 C10 C9 176.7(2) . . . . ?
C8 C9 C10 O2 -40.1(3) . . . . ?
C13 C9 C10 O2 83.5(3) . . . . ?
C8 C9 C10 O3 142.2(2) . . . . ?
C13 C9 C10 O3 -94.2(2) . . . . ?
C10 O3 C11 C12 -92.8(3) . . . . ?
C10 C9 C13 C14 -169.9(2) . . . . ?
C8 C9 C13 C14 -48.6(3) . . . . ?
C10 C9 C13 C15 67.8(3) . . . . ?
C8 C9 C13 C15 -171.0(2) . . . . ?
C14 C13 C15 C16 63.3(3) . . . . ?
C9 C13 C15 C16 -171.8(2) . . . . ?
C13 C15 C16 O5 55.2(4) . . . . ?
C13 C15 C16 O4 -125.9(3) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042

