# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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#######################################################################

data_ps171135
_database_code_depnum_ccdc_archive 'CCDC 1897155'
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-08-19 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 H18 O3'
_chemical_formula_weight         342.37

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   10.8534(4)
_cell_length_b                   13.6583(5)
_cell_length_c                   12.5256(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1856.78(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9156
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33166
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.397
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5665
_reflns_number_gt                3162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'PLATON(Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.0995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5665
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.26302(16) 0.43144(13) 0.62823(13) 0.0464(4) Uani 1 1 d . . . . .
O3 O 0.25251(18) 0.34081(14) 0.83017(17) 0.0579(5) Uani 1 1 d . . . . .
O2 O 0.2704(2) 0.48997(19) 0.9008(2) 0.0827(8) Uani 1 1 d . . . . .
C25 C 0.2494(2) 0.33474(18) 0.4813(2) 0.0422(6) Uani 1 1 d . . . . .
C26 C 0.0733(2) 0.33301(19) 0.36530(19) 0.0429(6) Uani 1 1 d . . . . .
C9 C 0.1897(2) 0.40398(18) 0.5440(2) 0.0404(6) Uani 1 1 d . . . . .
C12 C 0.3707(2) 0.37733(18) 0.6186(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.0172(2) 0.40267(19) 0.4314(2) 0.0456(6) Uani 1 1 d . . . . .
H7 H -0.061255 0.424878 0.414005 0.055 Uiso 1 1 calc R U . . .
C20 C 0.3119(3) 0.4244(2) 0.8491(2) 0.0528(7) Uani 1 1 d . . . . .
C10 C 0.1909(2) 0.2996(2) 0.3907(2) 0.0478(6) Uani 1 1 d . . . . .
H10 H 0.229879 0.254000 0.347161 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4660(3) 0.39597(19) 0.6985(2) 0.0459(6) Uani 1 1 d . . . . .
C8 C 0.0744(3) 0.4397(2) 0.5217(2) 0.0472(6) Uani 1 1 d . . . . .
H8 H 0.036622 0.486322 0.564829 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3671(3) 0.3198(2) 0.5316(2) 0.0515(7) Uani 1 1 d . . . . .
H11 H 0.429224 0.278052 0.508272 0.062 Uiso 1 1 calc R U . . .
C4 C 0.0056(3) 0.2947(2) 0.2713(2) 0.0475(7) Uani 1 1 d . . . . .
C19 C 0.4387(2) 0.42348(19) 0.8035(2) 0.0473(6) Uani 1 1 d . . . . .
C3 C -0.0793(3) 0.3516(2) 0.2170(2) 0.0581(8) Uani 1 1 d . . . . .
H3 H -0.093270 0.415712 0.238888 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5893(3) 0.3922(2) 0.6669(2) 0.0577(8) Uani 1 1 d . . . . .
H14 H 0.607857 0.372796 0.597587 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5347(3) 0.4505(2) 0.8710(3) 0.0631(8) Uani 1 1 d . . . . .
H18 H 0.517312 0.471874 0.939898 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6551(3) 0.4460(2) 0.8370(3) 0.0709(9) Uani 1 1 d . . . . .
H17 H 0.718003 0.463292 0.883740 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6845(3) 0.4162(2) 0.7348(3) 0.0656(8) Uani 1 1 d . . . . .
C5 C 0.0219(3) 0.1992(2) 0.2373(3) 0.0739(9) Uani 1 1 d . . . . .
H5 H 0.078450 0.159404 0.272479 0.089 Uiso 1 1 calc R U . . .
C21 C 0.1259(3) 0.3363(3) 0.8665(3) 0.0833(11) Uani 1 1 d . . . . .
H21A H 0.077796 0.384218 0.829043 0.125 Uiso 1 1 calc R U . . .
H21B H 0.122817 0.349363 0.941729 0.125 Uiso 1 1 calc R U . . .
H21C H 0.093218 0.272180 0.852715 0.125 Uiso 1 1 calc R U . . .
C2 C -0.1439(4) 0.3146(3) 0.1305(3) 0.0763(10) Uani 1 1 d . . . . .
H2 H -0.199529 0.354176 0.094077 0.092 Uiso 1 1 calc R U . . .
C1 C -0.1259(4) 0.2203(3) 0.0987(3) 0.1000(14) Uani 1 1 d . . . . .
H1 H -0.169100 0.195273 0.040670 0.120 Uiso 1 1 calc R U . . .
C6 C -0.0433(5) 0.1621(3) 0.1532(4) 0.1049(15) Uani 1 1 d . . . . .
H6 H -0.031958 0.097269 0.132567 0.126 Uiso 1 1 calc R U . . .
C16 C 0.8161(3) 0.4130(4) 0.6963(4) 0.1102(16) Uani 1 1 d . . . . .
H16A H 0.860822 0.364430 0.735860 0.165 Uiso 1 1 calc R U . . .
H16B H 0.853714 0.475932 0.706816 0.165 Uiso 1 1 calc R U . . .
H16C H 0.817606 0.396770 0.621761 0.165 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 C9 1.374(3) . ?
O1 C12 1.388(3) . ?
O3 C20 1.332(4) . ?
O3 C21 1.449(4) . ?
O2 C20 1.194(4) . ?
C25 C10 1.386(4) . ?
C25 C9 1.390(4) . ?
C25 C11 1.439(4) . ?
C26 C10 1.391(4) . ?
C26 C7 1.400(4) . ?
C26 C4 1.484(4) . ?
C9 C8 1.373(4) . ?
C12 C11 1.344(4) . ?
C12 C13 1.461(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9300 . ?
C20 C19 1.491(4) . ?
C10 H10 0.9300 . ?
C13 C14 1.397(4) . ?
C13 C19 1.399(4) . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C3 1.384(4) . ?
C19 C18 1.392(4) . ?
C3 C2 1.386(4) . ?
C3 H3 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C18 C17 1.376(5) . ?
C18 H18 0.9300 . ?
C17 C15 1.380(5) . ?
C17 H17 0.9300 . ?
C15 C16 1.508(5) . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C2 C1 1.363(5) . ?
C2 H2 0.9300 . ?
C1 C6 1.378(6) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C9 O1 C12 106.00(18) . . ?
C20 O3 C21 116.1(2) . . ?
C10 C25 C9 119.0(2) . . ?
C10 C25 C11 135.8(2) . . ?
C9 C25 C11 105.2(2) . . ?
C10 C26 C7 119.1(2) . . ?
C10 C26 C4 121.3(2) . . ?
C7 C26 C4 119.5(2) . . ?
C8 C9 O1 126.0(2) . . ?
C8 C9 C25 123.5(3) . . ?
O1 C9 C25 110.5(2) . . ?
C11 C12 O1 110.9(2) . . ?
C11 C12 C13 132.6(2) . . ?
O1 C12 C13 116.4(2) . . ?
C8 C7 C26 122.4(2) . . ?
C8 C7 H7 118.8 . . ?
C26 C7 H7 118.8 . . ?
O2 C20 O3 123.8(3) . . ?
O2 C20 C19 124.3(3) . . ?
O3 C20 C19 111.8(3) . . ?
C25 C10 C26 119.6(2) . . ?
C25 C10 H10 120.2 . . ?
C26 C10 H10 120.2 . . ?
C14 C13 C19 118.6(3) . . ?
C14 C13 C12 118.6(2) . . ?
C19 C13 C12 122.7(2) . . ?
C9 C8 C7 116.4(2) . . ?
C9 C8 H8 121.8 . . ?
C7 C8 H8 121.8 . . ?
C12 C11 C25 107.3(2) . . ?
C12 C11 H11 126.3 . . ?
C25 C11 H11 126.3 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 C26 120.8(3) . . ?
C3 C4 C26 121.5(3) . . ?
C18 C19 C13 119.0(3) . . ?
C18 C19 C20 117.1(3) . . ?
C13 C19 C20 123.9(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C15 C14 C13 122.4(3) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C17 C15 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C15 C17 H17 119.3 . . ?
C14 C15 C17 118.0(3) . . ?
C14 C15 C16 120.4(3) . . ?
C17 C15 C16 121.6(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044

