# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_s19sel16
_database_code_depnum_ccdc_archive 'CCDC 2047319'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-02-26 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         'C15 H16 O'
_chemical_formula_sum            'C15 H16 O'
_chemical_formula_weight         212.28

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.37310(10)
_cell_length_b                   6.72170(10)
_cell_length_c                   16.6660(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1162.03(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6355
_cell_measurement_theta_min      2.6700
_cell_measurement_theta_max      73.1970

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.493
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.572
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.956
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 -2 0.2462
-7 0 -1 0.0775
5 3 0 0.2120
1 0 -11 0.0213
7 0 -1 0.0625
3 0 10 0.0403
0 0 11 0.0424
-1 -4 1 0.2309
2 -4 3 0.2220
-7 0 0 0.0762
-6 0 4 0.0663
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
0.0927 4.2727 -2.1792 -0.7135 -0.1318 -0.6881
-6.6806 -0.0387 -1.3457 -0.6787 -0.1273 0.7233
4.8914 2.9989 -0.1792 -0.0041 0.0338 -0.9994
0.7976 -0.2800 -10.7218 0.0787 -0.9926 -0.0921
6.7039 0.0662 -0.9964 0.6657 -0.0882 -0.7410
2.8290 0.0692 9.8171 0.3209 0.9072 -0.2719
-0.1143 0.0743 10.8173 0.0255 0.9984 0.0507
-0.8197 -4.2975 1.3193 0.6398 0.0518 0.7668
2.0943 -4.0200 2.5087 0.8951 0.1671 0.4133
-6.7298 0.1114 0.1924 -0.7017 0.0169 0.7123
-6.1873 0.1944 4.2407 -0.6418 0.3917 0.6593
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.699
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            11287
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.022
_diffrn_reflns_theta_max         73.439
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1277
_reflns_number_gt                1218
_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       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_structure_solution    
; 
 SHELXS
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement  
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0755P)²+0.2638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1277
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O O 0.69586(11) 0.250000 0.67164(7) 0.0351(3) Uani 1 2 d S T P . .
C1 C 0.66145(16) 0.250000 0.60241(10) 0.0294(4) Uani 1 2 d S T P . .
H1 H 0.726507 0.250000 0.562288 0.035 Uiso 1 2 calc R U P . .
C2 C 0.52454(13) 0.250000 0.57519(9) 0.0230(4) Uani 1 2 d S T P . .
C3 C 0.43283(15) 0.250000 0.63662(8) 0.0255(4) Uani 1 2 d S T P . .
H3 H 0.467776 0.250000 0.689305 0.031 Uiso 1 2 calc R U P . .
C4 C 0.29920(14) 0.250000 0.63337(8) 0.0249(4) Uani 1 2 d S T P . .
H4 H 0.257846 0.250000 0.684227 0.030 Uiso 1 2 calc R U P . .
C5 C 0.21472(13) 0.250000 0.56737(9) 0.0234(4) Uani 1 2 d S T P . .
C6 C 0.07021(14) 0.250000 0.58539(9) 0.0277(4) Uani 1 2 d S T P . .
H6 H 0.023696 0.249999 0.532832 0.033 Uiso 1 2 calc R U P . .
C7 C 0.02902(11) 0.43593(19) 0.63091(8) 0.0383(3) Uani 1 1 d . . . . .
H7A H 0.054663 0.554368 0.600558 0.057 Uiso 1 1 calc R U . . .
H7B H 0.070715 0.437738 0.683672 0.057 Uiso 1 1 calc R U . . .
H7C H -0.064801 0.435313 0.637789 0.057 Uiso 1 1 calc R U . . .
C8 C 0.25125(14) 0.250000 0.48719(9) 0.0227(3) Uani 1 2 d S T P . .
H8 H 0.181673 0.250000 0.450123 0.027 Uiso 1 2 calc R U P . .
C9 C 0.37339(13) 0.250000 0.45219(9) 0.0214(3) Uani 1 2 d S T P . .
C10 C 0.39571(15) 0.250000 0.36919(8) 0.0247(4) Uani 1 2 d S T P . .
C11 C 0.29669(15) 0.250000 0.30386(9) 0.0286(4) Uani 1 2 d S T P . .
H11A H 0.224304 0.164622 0.319425 0.043 Uiso 0.5 1 calc R U P . .
H11B H 0.335315 0.199394 0.254234 0.043 Uiso 0.5 1 calc R U P . .
H11C H 0.265616 0.385984 0.295164 0.043 Uiso 0.5 1 calc R U P . .
C12 C 0.53035(16) 0.250000 0.35760(9) 0.0284(4) Uani 1 2 d S T P . .
H12 H 0.571367 0.250000 0.306630 0.034 Uiso 1 2 calc R U P . .
C13 C 0.59486(14) 0.250000 0.43027(9) 0.0270(4) Uani 1 2 d S T P . .
H13 H 0.685796 0.250000 0.437010 0.032 Uiso 1 2 calc R U P . .
C14 C 0.50307(14) 0.250000 0.49260(9) 0.0225(3) Uani 1 2 d S T P . .


_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
O C1 1.208(2) . ?
C1 C2 1.491(2) . ?
C1 H1 0.9500 . ?
C2 C14 1.394(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4 0.9500 . ?
C5 C8 1.389(2) . ?
C5 C6 1.5288(19) . ?
C6 C7 1.5231(15) . ?
C6 C7 1.5232(15) 7_565 ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.4025(19) . ?
C9 C14 1.5044(19) . ?
C10 C12 1.410(2) . ?
C10 C11 1.497(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11A 0.980(13) 7_565 ?
C11 H11B 0.980(9) 7_565 ?
C11 H11C 0.980(4) 7_565 ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(2) . ?
C13 H13 0.9500 . ?

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
O C1 C2 124.90(15) . . ?
O C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C14 C2 C3 127.91(13) . . ?
C14 C2 C1 116.90(13) . . ?
C3 C2 C1 115.19(13) . . ?
C4 C3 C2 130.66(13) . . ?
C4 C3 H3 114.7 . . ?
C2 C3 H3 114.7 . . ?
C3 C4 C5 130.78(13) . . ?
C3 C4 H4 114.6 . . ?
C5 C4 H4 114.6 . . ?
C8 C5 C4 125.62(13) . . ?
C8 C5 C6 117.16(13) . . ?
C4 C5 C6 117.21(12) . . ?
C7 C6 C7 110.27(13) . 7_565 ?
C7 C6 C5 111.89(8) . . ?
C7 C6 C5 111.89(8) 7_565 . ?
C7 C6 H6 107.5 . . ?
C7 C6 H6 107.5 7_565 . ?
C5 C6 H6 107.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 C9 130.56(14) . . ?
C5 C8 H8 114.7 . . ?
C9 C8 H8 114.7 . . ?
C8 C9 C10 124.22(14) . . ?
C8 C9 C14 128.68(13) . . ?
C10 C9 C14 107.09(12) . . ?
C9 C10 C12 107.38(13) . . ?
C9 C10 C11 127.16(14) . . ?
C12 C10 C11 125.46(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5(3) . 7_565 ?
H11A C11 H11A 71.7 . 7_565 ?
H11B C11 H11A 137.7 . 7_565 ?
C10 C11 H11B 109.5(2) . 7_565 ?
H11A C11 H11B 137.7 . 7_565 ?
H11C C11 H11B 71.7 . 7_565 ?
H11A C11 H11B 109.5 7_565 7_565 ?
C10 C11 H11C 109.47(8) . 7_565 ?
H11B C11 H11C 71.7 . 7_565 ?
H11C C11 H11C 137.7 . 7_565 ?
H11A C11 H11C 109.5 7_565 7_565 ?
H11B C11 H11C 109.5 7_565 7_565 ?
C13 C12 C10 111.05(13) . . ?
C13 C12 H12 124.5 . . ?
C10 C12 H12 124.5 . . ?
C12 C13 C14 108.57(13) . . ?
C12 C13 H13 125.7 . . ?
C14 C13 H13 125.7 . . ?
C2 C14 C13 128.30(14) . . ?
C2 C14 C9 125.78(13) . . ?
C13 C14 C9 105.91(13) . . ?

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
O C1 C2 C14 180.000(0) . . . . ?
O C1 C2 C3 0.000(0) . . . . ?
C14 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C8 0.000(1) . . . . ?
C3 C4 C5 C6 180.000(0) . . . . ?
C8 C5 C6 C7 -117.84(9) . . . . ?
C4 C5 C6 C7 62.16(9) . . . . ?
C8 C5 C6 C7 117.84(9) . . . 7_565 ?
C4 C5 C6 C7 -62.16(9) . . . 7_565 ?
C4 C5 C8 C9 0.000(1) . . . . ?
C6 C5 C8 C9 180.000(0) . . . . ?
C5 C8 C9 C10 180.000(0) . . . . ?
C5 C8 C9 C14 0.000(0) . . . . ?
C8 C9 C10 C12 180.000(0) . . . . ?
C14 C9 C10 C12 0.000(0) . . . . ?
C8 C9 C10 C11 0.000(0) . . . . ?
C14 C9 C10 C11 180.000(0) . . . . ?
C9 C10 C12 C13 0.000(0) . . . . ?
C11 C10 C12 C13 180.000(0) . . . . ?
C10 C12 C13 C14 0.000(0) . . . . ?
C3 C2 C14 C13 180.000(0) . . . . ?
C1 C2 C14 C13 0.000(0) . . . . ?
C3 C2 C14 C9 0.000(0) . . . . ?
C1 C2 C14 C9 180.000(0) . . . . ?
C12 C13 C14 C2 180.000(0) . . . . ?
C12 C13 C14 C9 0.000(0) . . . . ?
C8 C9 C14 C2 0.000(0) . . . . ?
C10 C9 C14 C2 180.000(0) . . . . ?
C8 C9 C14 C13 180.000(0) . . . . ?
C10 C9 C14 C13 0.000(0) . . . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.064

