# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2019sot0006_k1_100k
_database_code_depnum_ccdc_archive 'CCDC 1908866'
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
light@soton.ac.uk
ws2g13@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 O5'
_chemical_oxdiff_usercomment     SW/8311/143
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1160(3)
_cell_length_b                   9.3511(3)
_cell_length_c                   9.7170(3)
_cell_angle_alpha                88.072(2)
_cell_angle_beta                 65.610(3)
_cell_angle_gamma                66.567(3)
_cell_volume                     683.68(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14192
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5530
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0843
0 0 1 0.0843
-5 -1 -2 0.2028
5 1 2 0.2028
-1 -5 0 0.2129
1 5 0 0.2129
4 5 1 0.1022

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.169
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.0000 -0.9985 -0.0785 -0.0165 0.0118
0.0000 0.0000 0.9985 0.0785 0.0165 -0.0118
-4.9945 -0.9994 -1.9970 -0.0224 -0.0297 -0.3974
4.9945 0.9994 1.9970 0.0224 0.0297 0.3974
-0.9985 -4.9928 -0.0003 -0.1056 0.3728 -0.0142
0.9985 4.9928 0.0003 0.1056 -0.3728 0.0142
3.9952 4.9934 0.9987 0.0868 -0.3118 0.2637

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20674
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         3.050
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00  17.00   1.00    1.00    --  -19.30 -60.00 150.00  126
  2  ω   -109.00  17.00   1.00    1.00    --  -19.30 -60.00  30.00  126
  3  ω    -56.00  70.00   1.00    1.00    --  -19.30  60.00-120.00  126
  4  ω    -56.00  70.00   1.00    1.00    --  -19.30  60.00  30.00  126
  5  ω    -56.00  70.00   1.00    1.00    --  -19.30  60.00 120.00  126
  6  ω   -109.00  17.00   1.00    1.00    --  -19.30 -60.00 -90.00  126
  7  ω    -56.00  70.00   1.00    1.00    --  -19.30  60.00 -30.00  126
  8  ω   -109.00  16.00   1.00    1.00    --  -19.30 -57.00 -60.00  125
  9  ω    -56.00  38.00   1.00    1.00    --  -19.30  60.00  60.00   94
 10  ω    -56.00  70.00   1.00    1.00    --  -19.30  60.00-180.00  126
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0324624000
_diffrn_orient_matrix_UB_12      0.0276409000
_diffrn_orient_matrix_UB_13      0.0785702000
_diffrn_orient_matrix_UB_21      0.0148783000
_diffrn_orient_matrix_UB_22      -0.0776428000
_diffrn_orient_matrix_UB_23      0.0165145000
_diffrn_orient_matrix_UB_31      0.0871878000
_diffrn_orient_matrix_UB_32      -0.0145944000
_diffrn_orient_matrix_UB_33      -0.0117732000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3335
_reflns_number_total             3457
_reflns_odcompleteness_completeness 95.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.2268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.96842(10) 0.24059(9) 0.54524(8) 0.02238(17) Uani 1 1 d . . . . .
O2 O 0.26751(9) 0.86200(8) 0.61703(8) 0.02047(16) Uani 1 1 d . . . . .
O3 O 0.50427(9) 0.81060(8) 0.39022(8) 0.01767(15) Uani 1 1 d . . . . .
O4 O 0.70896(9) 0.61361(8) 0.18175(7) 0.01568(15) Uani 1 1 d . . . . .
O5 O 0.81173(11) 0.61756(9) -0.06929(8) 0.02435(17) Uani 1 1 d . . . . .
C1 C 1.12554(15) 0.16703(14) 0.40497(13) 0.0302(3) Uani 1 1 d . . . . .
H1A H 1.093378 0.144545 0.326250 0.045 Uiso 1 1 calc GR . . . .
H1B H 1.206137 0.068241 0.420751 0.045 Uiso 1 1 calc GR . . . .
H1C H 1.184656 0.237951 0.371902 0.045 Uiso 1 1 calc GR . . . .
C2 C 0.83785(13) 0.37581(11) 0.54311(11) 0.01690(19) Uani 1 1 d . . . . .
C3 C 0.67846(13) 0.43150(11) 0.68138(11) 0.01675(19) Uani 1 1 d . . . . .
C4 C 0.66864(14) 0.34099(13) 0.81343(12) 0.0226(2) Uani 1 1 d . . . . .
H4A H 0.749324 0.347469 0.852802 0.034 Uiso 1 1 calc GR . . . .
H4B H 0.703362 0.230265 0.778791 0.034 Uiso 1 1 calc GR . . . .
H4C H 0.546832 0.386288 0.894729 0.034 Uiso 1 1 calc GR . . . .
C5 C 0.53508(13) 0.56637(11) 0.68940(10) 0.01646(19) Uani 1 1 d . . . . .
H5 H 0.426768 0.605909 0.780230 0.020 Uiso 1 1 calc R . . . .
C6 C 0.55229(12) 0.64324(11) 0.56191(10) 0.01536(18) Uani 1 1 d . . . . .
C7 C 0.70946(12) 0.58887(11) 0.43006(10) 0.01488(18) Uani 1 1 d . . . . .
C8 C 0.85663(13) 0.45461(11) 0.41627(10) 0.01632(18) Uani 1 1 d . . . . .
H8 H 0.964797 0.417901 0.325331 0.020 Uiso 1 1 calc R . . . .
C9 C 0.42090(13) 0.78065(11) 0.53625(11) 0.01633(18) Uani 1 1 d . . . . .
C10 C 0.68757(12) 0.69677(10) 0.31506(10) 0.01487(18) Uani 1 1 d . . . . .
C11 C 0.81202(13) 0.77800(11) 0.25425(10) 0.01648(18) Uani 1 1 d . . . . .
H11A H 0.930510 0.710110 0.248507 0.020 Uiso 1 1 calc R . . . .
H11B H 0.763195 0.879516 0.320282 0.020 Uiso 1 1 calc R . . . .
C12 C 0.82343(12) 0.80485(11) 0.09406(10) 0.01602(18) Uani 1 1 d . . . . .
C13 C 0.78491(12) 0.67208(11) 0.05330(11) 0.01652(19) Uani 1 1 d . . . . .
C14 C 0.67798(14) 0.96270(12) 0.09562(12) 0.0224(2) Uani 1 1 d . . . . .
H14A H 0.682072 0.968301 -0.006717 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.697809 1.050014 0.125522 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.561386 0.970378 0.169046 0.034 Uiso 1 1 calc GR . . . .
C15 C 1.00742(13) 0.78786(12) -0.02033(11) 0.0206(2) Uani 1 1 d . . . . .
H15A H 1.095783 0.681023 -0.029778 0.031 Uiso 1 1 calc GR . . . .
H15B H 1.036692 0.864947 0.015687 0.031 Uiso 1 1 calc GR . . . .
H15C H 1.007803 0.806712 -0.120273 0.031 Uiso 1 1 calc GR . . . .


_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 C1 1.4316(13) . ?
O1 C2 1.3555(11) . ?
O2 C9 1.1990(12) . ?
O3 C9 1.3862(11) . ?
O3 C10 1.4451(11) . ?
O4 C10 1.4350(11) . ?
O4 C13 1.3703(11) . ?
O5 C13 1.1999(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4215(13) . ?
C2 C8 1.3987(12) . ?
C3 C4 1.5044(13) . ?
C3 C5 1.3843(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.3947(13) . ?
C6 C7 1.3789(13) . ?
C6 C9 1.4659(13) . ?
C7 C8 1.3847(13) . ?
C7 C10 1.5016(12) . ?
C8 H8 0.9500 . ?
C10 C11 1.5214(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5354(13) . ?
C12 C13 1.5219(13) . ?
C12 C14 1.5380(13) . ?
C12 C15 1.5278(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C2 O1 C1 117.64(8) . . ?
C9 O3 C10 110.70(7) . . ?
C13 O4 C10 110.63(7) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 114.27(8) . . ?
O1 C2 C8 123.34(9) . . ?
C8 C2 C3 122.39(9) . . ?
C2 C3 C4 119.36(9) . . ?
C5 C3 C2 118.79(8) . . ?
C5 C3 C4 121.84(9) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5 120.6 . . ?
C3 C5 C6 118.90(9) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C9 130.19(9) . . ?
C7 C6 C5 121.28(9) . . ?
C7 C6 C9 108.48(8) . . ?
C6 C7 C8 122.04(8) . . ?
C6 C7 C10 108.82(8) . . ?
C8 C7 C10 129.13(8) . . ?
C2 C8 H8 121.7 . . ?
C7 C8 C2 116.57(8) . . ?
C7 C8 H8 121.7 . . ?
O2 C9 O3 120.86(9) . . ?
O2 C9 C6 131.42(9) . . ?
O3 C9 C6 107.71(8) . . ?
O3 C10 C7 104.20(7) . . ?
O3 C10 C11 111.22(7) . . ?
O4 C10 O3 107.20(7) . . ?
O4 C10 C7 110.82(7) . . ?
O4 C10 C11 105.08(7) . . ?
C7 C10 C11 117.98(8) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C10 C11 C12 104.22(7) . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C11 C12 C14 112.76(8) . . ?
C13 C12 C11 101.16(7) . . ?
C13 C12 C14 108.18(8) . . ?
C13 C12 C15 110.70(8) . . ?
C15 C12 C11 112.53(8) . . ?
C15 C12 C14 111.02(8) . . ?
O4 C13 C12 110.58(8) . . ?
O5 C13 O4 120.04(9) . . ?
O5 C13 C12 129.38(9) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_date_sample_data_collection 2019-04-01
_olex2_date_sample_submission    2019-03-25
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder silicon oil'
_olex2_submission_original_sample_id SW/8311/143
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.589
