# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_glo9287
_database_code_depnum_ccdc_archive 'CCDC 1866187'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch-Chemisches Institut, WWU University of M?nster
Germany
;
_audit_update_record             
;
2018-09-06 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         278.33

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   8.2948(3)
_cell_length_b                   9.5359(3)
_cell_length_c                   10.0158(3)
_cell_angle_alpha                75.291(2)
_cell_angle_beta                 74.899(2)
_cell_angle_gamma                86.594(2)
_cell_volume                     739.79(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4486
_cell_measurement_theta_min      4.7197
_cell_measurement_theta_max      66.5941
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10704
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         66.64
_diffrn_reflns_theta_full        66.64
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_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_number_total             2564
_reflns_number_gt                2025
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1113
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         2564
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.1586P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.07951(13) 0.23459(13) 0.58642(11) 0.0245(3) Uani d . . . 1 . .
O O2 -0.00377(13) 0.18127(13) 0.82007(11) 0.0276(3) Uani d . . . 1 . .
C C1 0.11564(19) 0.20397(17) 0.71717(16) 0.0220(3) Uani d . . . 1 . .
C C2 0.29186(19) 0.20246(16) 0.71758(16) 0.0206(3) Uani d . . . 1 . .
C C3 0.3400(2) 0.17221(17) 0.84827(16) 0.0216(3) Uani d . . . 1 . .
C C4 0.5093(2) 0.16864(18) 0.84121(17) 0.0251(4) Uani d . . . 1 . .
H H4 0.544 0.1478 0.9274 0.03 Uiso calc U . R 1 . .
C C5 0.6302(2) 0.19473(18) 0.71146(18) 0.0260(4) Uani d . . . 1 . .
H H5 0.7453 0.1906 0.7104 0.031 Uiso calc U . R 1 . .
C C6 0.58370(19) 0.22654(18) 0.58456(17) 0.0237(4) Uani d . . . 1 . .
H H6 0.6667 0.2461 0.4965 0.028 Uiso calc U . R 1 . .
C C7 0.41467(19) 0.23008(16) 0.58516(16) 0.0208(3) Uani d . . . 1 . .
C C8 0.36269(19) 0.26189(17) 0.45195(16) 0.0209(3) Uani d . . . 1 . .
C C9 0.19943(19) 0.26326(17) 0.45760(16) 0.0223(4) Uani d . . . 1 . .
C C10 0.2174(2) 0.14776(19) 0.99251(17) 0.0268(4) Uani d . . . 1 . .
H H10A 0.278 0.1384 1.0663 0.04 Uiso calc U . R 1 . .
H H10B 0.1532 0.0588 1.0108 0.04 Uiso calc U . R 1 . .
H H10C 0.1412 0.2302 0.9943 0.04 Uiso calc U . R 1 . .
C C11 0.49173(19) 0.29302(18) 0.31239(16) 0.0214(4) Uani d . . . 1 . .
C C12 0.5285(2) 0.43482(19) 0.23356(17) 0.0290(4) Uani d . . . 1 . .
H H12 0.4717 0.5127 0.2688 0.035 Uiso calc U . R 1 . .
C C13 0.6476(2) 0.4636(2) 0.10345(19) 0.0336(4) Uani d . . . 1 . .
H H13 0.6704 0.561 0.0495 0.04 Uiso calc U . R 1 . .
C C14 0.7336(2) 0.3513(2) 0.05191(17) 0.0280(4) Uani d . . . 1 . .
H H14 0.8158 0.3712 -0.0367 0.034 Uiso calc U . R 1 . .
C C15 0.6985(2) 0.21006(19) 0.13071(17) 0.0264(4) Uani d . . . 1 . .
H H15 0.7575 0.1325 0.0965 0.032 Uiso calc U . R 1 . .
C C16 0.5776(2) 0.18091(18) 0.25946(17) 0.0254(4) Uani d . . . 1 . .
H H16 0.5532 0.0833 0.312 0.031 Uiso calc U . R 1 . .
C C17 0.1186(2) 0.29061(19) 0.33529(16) 0.0252(4) Uani d . . . 1 . .
H H17 0.2095 0.3097 0.2448 0.03 Uiso calc U . R 1 . .
C C18 0.0078(2) 0.4249(2) 0.33146(18) 0.0316(4) Uani d . . . 1 . .
H H18A -0.0796 0.4109 0.421 0.047 Uiso calc U . R 1 . .
H H18B -0.0438 0.4398 0.2514 0.047 Uiso calc U . R 1 . .
H H18C 0.0758 0.5099 0.3195 0.047 Uiso calc U . R 1 . .
C C19 0.0216(2) 0.1562(2) 0.34188(18) 0.0296(4) Uani d . . . 1 . .
H H19A 0.0986 0.0748 0.335 0.044 Uiso calc U . R 1 . .
H H19B -0.0315 0.1765 0.2624 0.044 Uiso calc U . R 1 . .
H H19C -0.0642 0.1314 0.4324 0.044 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3748(19) ?
O1 C9 . 1.3833(18) ?
O2 C1 . 1.2126(18) ?
C1 C2 . 1.462(2) ?
C2 C7 . 1.420(2) ?
C2 C3 . 1.422(2) ?
C3 C4 . 1.386(2) ?
C3 C10 . 1.506(2) ?
C4 C5 . 1.394(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.379(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.399(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.462(2) ?
C8 C9 . 1.340(2) ?
C8 C11 . 1.495(2) ?
C9 C17 . 1.505(2) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.388(2) ?
C11 C16 . 1.390(2) ?
C12 C13 . 1.389(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.387(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 C18 . 1.529(2) ?
C17 C19 . 1.532(2) ?
C17 H17 . 1.0 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C9 . . 123.82(12) ?
O2 C1 O1 . . 115.72(14) ?
O2 C1 C2 . . 127.17(14) ?
O1 C1 C2 . . 117.11(13) ?
C7 C2 C3 . . 120.40(14) ?
C7 C2 C1 . . 118.89(14) ?
C3 C2 C1 . . 120.71(14) ?
C4 C3 C2 . . 117.77(14) ?
C4 C3 C10 . . 118.66(14) ?
C2 C3 C10 . . 123.55(14) ?
C3 C4 C5 . . 121.97(15) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C6 C5 C4 . . 120.32(15) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 120.22(14) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C6 C7 C2 . . 119.30(14) ?
C6 C7 C8 . . 121.10(14) ?
C2 C7 C8 . . 119.60(14) ?
C9 C8 C7 . . 119.07(14) ?
C9 C8 C11 . . 121.25(14) ?
C7 C8 C11 . . 119.68(13) ?
C8 C9 O1 . . 121.49(14) ?
C8 C9 C17 . . 128.06(14) ?
O1 C9 C17 . . 110.44(13) ?
C3 C10 H10A . . 109.5 ?
C3 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C3 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 118.78(14) ?
C12 C11 C8 . . 120.46(15) ?
C16 C11 C8 . . 120.76(14) ?
C11 C12 C13 . . 120.43(16) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.44(16) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.29(15) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 120.37(16) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C11 . . 120.68(15) ?
C15 C16 H16 . . 119.7 ?
C11 C16 H16 . . 119.7 ?
C9 C17 C18 . . 111.17(13) ?
C9 C17 C19 . . 110.61(14) ?
C18 C17 C19 . . 111.79(14) ?
C9 C17 H17 . . 107.7 ?
C18 C17 H17 . . 107.7 ?
C19 C17 H17 . . 107.7 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 O1 C1 O2 . . . . -179.99(14) ?
C9 O1 C1 C2 . . . . 0.1(2) ?
O2 C1 C2 C7 . . . . 179.19(15) ?
O1 C1 C2 C7 . . . . -0.9(2) ?
O2 C1 C2 C3 . . . . -0.1(3) ?
O1 C1 C2 C3 . . . . 179.80(14) ?
C7 C2 C3 C4 . . . . -1.0(2) ?
C1 C2 C3 C4 . . . . 178.30(14) ?
C7 C2 C3 C10 . . . . 177.47(14) ?
C1 C2 C3 C10 . . . . -3.3(2) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C10 C3 C4 C5 . . . . -177.97(15) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C4 C5 C6 C7 . . . . -1.2(2) ?
C5 C6 C7 C2 . . . . 0.8(2) ?
C5 C6 C7 C8 . . . . -179.28(15) ?
C3 C2 C7 C6 . . . . 0.3(2) ?
C1 C2 C7 C6 . . . . -178.97(14) ?
C3 C2 C7 C8 . . . . -179.60(14) ?
C1 C2 C7 C8 . . . . 1.1(2) ?
C6 C7 C8 C9 . . . . 179.59(15) ?
C2 C7 C8 C9 . . . . -0.5(2) ?
C6 C7 C8 C11 . . . . -0.8(2) ?
C2 C7 C8 C11 . . . . 179.15(14) ?
C7 C8 C9 O1 . . . . -0.3(2) ?
C11 C8 C9 O1 . . . . -179.97(14) ?
C7 C8 C9 C17 . . . . -178.89(15) ?
C11 C8 C9 C17 . . . . 1.5(3) ?
C1 O1 C9 C8 . . . . 0.5(2) ?
C1 O1 C9 C17 . . . . 179.32(14) ?
C9 C8 C11 C12 . . . . 79.9(2) ?
C7 C8 C11 C12 . . . . -99.77(19) ?
C9 C8 C11 C16 . . . . -100.41(19) ?
C7 C8 C11 C16 . . . . 79.94(19) ?
C16 C11 C12 C13 . . . . 0.7(3) ?
C8 C11 C12 C13 . . . . -179.60(15) ?
C11 C12 C13 C14 . . . . -1.2(3) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
C13 C14 C15 C16 . . . . 0.5(3) ?
C14 C15 C16 C11 . . . . -1.0(2) ?
C12 C11 C16 C15 . . . . 0.4(2) ?
C8 C11 C16 C15 . . . . -179.31(14) ?
C8 C9 C17 C18 . . . . -118.47(18) ?
O1 C9 C17 C18 . . . . 62.84(17) ?
C8 C9 C17 C19 . . . . 116.71(18) ?
O1 C9 C17 C19 . . . . -61.98(17) ?

