# 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_DS_B1_0032
_database_code_depnum_ccdc_archive 'CCDC 1986749'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2020-02-27 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Thomas Osberger'
_cambridge_user_crsid            jo394
_cambridge_supervisor_name       'David Spring'
_cambridge_supervisor_crsid      drs36
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             TO3078
_cambridge_data_id               DS_B1_0032

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.1906(5)
_cell_length_b                   6.2367(2)
_cell_length_c                   21.3876(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.3105(14)
_cell_angle_gamma                90
_cell_volume                     2121.36(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6479
_cell_measurement_theta_min      5.56
_cell_measurement_theta_max      66.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11799
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.469
_diffrn_reflns_theta_max         66.722
_diffrn_reflns_theta_full        66.722
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1872
_reflns_number_gt                1576
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0445P)²+1.4461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.044

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 0.71841(7) 0.14009(19) 0.41760(6) 0.0396(3) Uani 1 1 d . . . . .
O2 O 0.61375(7) 0.26681(18) 0.44377(5) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.61576(7) 0.17446(18) 0.09702(5) 0.0310(3) Uani 1 1 d . . . . .
C1 C 0.67967(9) 0.2933(3) 0.42445(7) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.69377(9) 0.5261(2) 0.41457(7) 0.0255(3) Uani 1 1 d . . . . .
H2A H 0.751510 0.579490 0.442206 0.031 Uiso 1 1 calc R U . . .
C3 C 0.65633(9) 0.6137(2) 0.34009(7) 0.0250(3) Uani 1 1 d . . . . .
H3A H 0.686536 0.749624 0.338750 0.030 Uiso 1 1 calc R U . . .
C4 C 0.57536(9) 0.6741(3) 0.35181(7) 0.0307(4) Uani 1 1 d . . . . .
H4A H 0.556860 0.823847 0.339256 0.037 Uiso 1 1 calc R U . . .
H4B H 0.528304 0.572722 0.330858 0.037 Uiso 1 1 calc R U . . .
C5 C 0.62222(9) 0.6404(3) 0.42861(7) 0.0278(3) Uani 1 1 d . . . . .
H5A H 0.639660 0.776189 0.455161 0.033 Uiso 1 1 calc R U . . .
C6 C 0.58692(10) 0.4724(3) 0.46131(8) 0.0323(4) Uani 1 1 d . . . . .
H6A H 0.609186 0.491844 0.510958 0.039 Uiso 1 1 calc R U . . .
H6B H 0.524791 0.481154 0.443797 0.039 Uiso 1 1 calc R U . . .
C7 C 0.64861(8) 0.4837(2) 0.27872(7) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.60842(8) 0.2853(2) 0.26422(7) 0.0244(3) Uani 1 1 d . . . . .
H8A H 0.588449 0.223207 0.295874 0.029 Uiso 1 1 calc R U . . .
C9 C 0.59674(8) 0.1758(2) 0.20479(7) 0.0249(3) Uani 1 1 d . . . . .
H9A H 0.569629 0.040092 0.196306 0.030 Uiso 1 1 calc R U . . .
C10 C 0.62496(8) 0.2660(2) 0.15777(7) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.66593(8) 0.4628(2) 0.17149(7) 0.0241(3) Uani 1 1 d . . . . .
H11A H 0.685991 0.524537 0.139840 0.029 Uiso 1 1 calc R U . . .
C12 C 0.67749(8) 0.5686(2) 0.23099(7) 0.0232(3) Uani 1 1 d . . . . .
H12A H 0.705829 0.702701 0.239758 0.028 Uiso 1 1 calc R U . . .
C13 C 0.58021(13) -0.0337(3) 0.08376(9) 0.0423(4) Uani 1 1 d . . . . .
H13A H 0.580929 -0.085811 0.040747 0.063 Uiso 1 1 calc R U . . .
H13B H 0.522080 -0.028442 0.081134 0.063 Uiso 1 1 calc R U . . .
H13C H 0.613058 -0.130967 0.120226 0.063 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
O1 C1 1.2052(18) . ?
O2 C1 1.3557(18) . ?
O2 C6 1.4590(19) . ?
O3 C10 1.3722(17) . ?
O3 C13 1.417(2) . ?
C1 C2 1.500(2) . ?
C2 C5 1.547(2) . ?
C2 C3 1.5721(19) . ?
C2 H2A 1.0000 . ?
C3 C7 1.5052(19) . ?
C3 C4 1.551(2) . ?
C3 H3A 1.0000 . ?
C4 C5 1.545(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.509(2) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.394(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.389(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(2) . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 O2 C6 110.71(12) . . ?
C10 O3 C13 117.16(12) . . ?
O1 C1 O2 120.31(15) . . ?
O1 C1 C2 128.62(14) . . ?
O2 C1 C2 111.07(12) . . ?
C1 C2 C5 103.64(12) . . ?
C1 C2 C3 116.95(12) . . ?
C5 C2 C3 89.24(11) . . ?
C1 C2 H2A 114.6 . . ?
C5 C2 H2A 114.6 . . ?
C3 C2 H2A 114.6 . . ?
C7 C3 C4 118.95(12) . . ?
C7 C3 C2 124.26(12) . . ?
C4 C3 C2 88.17(10) . . ?
C7 C3 H3A 107.8 . . ?
C4 C3 H3A 107.8 . . ?
C2 C3 H3A 107.8 . . ?
C5 C4 C3 90.06(11) . . ?
C5 C4 H4A 113.6 . . ?
C3 C4 H4A 113.6 . . ?
C5 C4 H4B 113.6 . . ?
C3 C4 H4B 113.6 . . ?
H4A C4 H4B 110.9 . . ?
C6 C5 C4 116.63(13) . . ?
C6 C5 C2 105.03(12) . . ?
C4 C5 C2 89.33(11) . . ?
C6 C5 H5A 114.3 . . ?
C4 C5 H5A 114.3 . . ?
C2 C5 H5A 114.3 . . ?
O2 C6 C5 105.61(11) . . ?
O2 C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
O2 C6 H6B 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
C8 C7 C12 117.21(13) . . ?
C8 C7 C3 123.00(12) . . ?
C12 C7 C3 119.65(13) . . ?
C9 C8 C7 121.83(13) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C8 C9 C10 119.63(13) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
O3 C10 C11 115.73(12) . . ?
O3 C10 C9 124.77(13) . . ?
C11 C10 C9 119.50(13) . . ?
C12 C11 C10 120.08(13) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C7 121.73(13) . . ?
C11 C12 H12A 119.1 . . ?
C7 C12 H12A 119.1 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C6 O2 C1 O1 169.07(13) . . . . ?
C6 O2 C1 C2 -10.71(16) . . . . ?
O1 C1 C2 C5 178.13(14) . . . . ?
O2 C1 C2 C5 -2.11(15) . . . . ?
O1 C1 C2 C3 81.93(19) . . . . ?
O2 C1 C2 C3 -98.31(14) . . . . ?
C1 C2 C3 C7 -32.82(19) . . . . ?
C5 C2 C3 C7 -137.75(13) . . . . ?
C1 C2 C3 C4 91.54(14) . . . . ?
C5 C2 C3 C4 -13.40(11) . . . . ?
C7 C3 C4 C5 142.17(13) . . . . ?
C2 C3 C4 C5 13.41(12) . . . . ?
C3 C4 C5 C6 -120.15(14) . . . . ?
C3 C4 C5 C2 -13.63(12) . . . . ?
C1 C2 C5 C6 13.30(15) . . . . ?
C3 C2 C5 C6 130.90(12) . . . . ?
C1 C2 C5 C4 -104.14(12) . . . . ?
C3 C2 C5 C4 13.45(11) . . . . ?
C1 O2 C6 C5 19.20(16) . . . . ?
C4 C5 C6 O2 77.51(15) . . . . ?
C2 C5 C6 O2 -19.44(15) . . . . ?
C4 C3 C7 C8 -55.90(19) . . . . ?
C2 C3 C7 C8 53.53(19) . . . . ?
C4 C3 C7 C12 119.61(15) . . . . ?
C2 C3 C7 C12 -130.96(14) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C3 C7 C8 C9 175.20(13) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C13 O3 C10 C11 175.18(13) . . . . ?
C13 O3 C10 C9 -4.7(2) . . . . ?
C8 C9 C10 O3 -178.92(12) . . . . ?
C8 C9 C10 C11 1.2(2) . . . . ?
O3 C10 C11 C12 179.35(12) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C3 C7 C12 C11 -174.90(12) . . . . ?



