# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1494610'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/C

loop_
_symmetry_equiv_pos_as_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                   28.543(6)
_cell_length_b                   7.3090(15)
_cell_length_c                   16.361(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.04(3)
_cell_angle_gamma                90.00
_cell_volume                     3296.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3093
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3030
_reflns_number_gt                1406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3030
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18763(8) 0.1838(3) 0.73903(15) 0.0630(7) Uani 1 1 d . . .
C1 C 0.13866(13) 0.1557(4) 0.71559(19) 0.0461(9) Uani 1 1 d . . .
O2 O 0.17949(8) 0.7584(3) 0.58619(16) 0.0746(8) Uani 1 1 d . . .
C2 C 0.11580(14) 0.0075(5) 0.7415(2) 0.0563(10) Uani 1 1 d . . .
H2A H 0.1340 -0.0819 0.7762 0.068 Uiso 1 1 calc R . .
O3 O 0.18888(9) 1.3246(3) 0.43949(16) 0.0693(8) Uani 1 1 d . . .
C3 C 0.06585(15) -0.0067(5) 0.7156(2) 0.0605(10) Uani 1 1 d . . .
H3A H 0.0506 -0.1060 0.7332 0.073 Uiso 1 1 calc R . .
C4 C 0.03853(13) 0.1234(5) 0.6644(2) 0.0568(10) Uani 1 1 d . . .
H4A H 0.0049 0.1131 0.6469 0.068 Uiso 1 1 calc R . .
C5 C 0.06193(12) 0.2706(5) 0.6393(2) 0.0484(9) Uani 1 1 d . . .
H5A H 0.0434 0.3587 0.6043 0.058 Uiso 1 1 calc R . .
C6 C 0.11176(11) 0.2919(4) 0.66432(18) 0.0391(8) Uani 1 1 d . . .
C7 C 0.13818(11) 0.4544(4) 0.6403(2) 0.0460(9) Uani 1 1 d . . .
H7A H 0.1571 0.5113 0.6919 0.055 Uiso 1 1 calc R . .
H7B H 0.1608 0.4096 0.6098 0.055 Uiso 1 1 calc R . .
C8 C 0.10703(11) 0.5998(4) 0.5870(2) 0.0448(8) Uani 1 1 d . . .
H8A H 0.0876 0.5439 0.5355 0.054 Uiso 1 1 calc R . .
H8B H 0.0850 0.6486 0.6178 0.054 Uiso 1 1 calc R . .
C9 C 0.13577(12) 0.7549(5) 0.5637(2) 0.0455(8) Uani 1 1 d . . .
C10 C 0.10686(11) 0.9059(4) 0.51194(19) 0.0440(8) Uani 1 1 d . . .
H10A H 0.0858 0.9598 0.5434 0.053 Uiso 1 1 calc R . .
H10B H 0.0864 0.8543 0.4603 0.053 Uiso 1 1 calc R . .
C11 C 0.13826(11) 1.0547(4) 0.4892(2) 0.0482(9) Uani 1 1 d . . .
H11A H 0.1594 1.1019 0.5412 0.058 Uiso 1 1 calc R . .
H11B H 0.1588 0.9995 0.4571 0.058 Uiso 1 1 calc R . .
C12 C 0.11202(12) 1.2138(4) 0.43911(18) 0.0416(8) Uani 1 1 d . . .
C13 C 0.06233(12) 1.2340(5) 0.4153(2) 0.0489(9) Uani 1 1 d . . .
H13A H 0.0431 1.1461 0.4318 0.059 Uiso 1 1 calc R . .
C14 C 0.04030(13) 1.3817(5) 0.3675(2) 0.0574(10) Uani 1 1 d . . .
H14A H 0.0067 1.3913 0.3518 0.069 Uiso 1 1 calc R . .
C15 C 0.06788(15) 1.5133(5) 0.3434(2) 0.0608(10) Uani 1 1 d . . .
H15A H 0.0530 1.6122 0.3112 0.073 Uiso 1 1 calc R . .
C16 C 0.11794(15) 1.4995(5) 0.3670(2) 0.0591(10) Uani 1 1 d . . .
H16A H 0.1368 1.5901 0.3512 0.071 Uiso 1 1 calc R . .
C17 C 0.14007(13) 1.3506(5) 0.4142(2) 0.0491(9) Uani 1 1 d . . .
C18 C 0.21794(13) 0.0469(5) 0.7880(3) 0.0859(14) Uani 1 1 d . . .
H18A H 0.2512 0.0847 0.7994 0.129 Uiso 1 1 calc R . .
H18B H 0.2137 -0.0662 0.7571 0.129 Uiso 1 1 calc R . .
H18C H 0.2093 0.0300 0.8404 0.129 Uiso 1 1 calc R . .
C19 C 0.22007(14) 1.4630(6) 0.4217(3) 0.0983(16) Uani 1 1 d . . .
H19A H 0.2533 1.4258 0.4433 0.147 Uiso 1 1 calc R . .
H19B H 0.2147 1.5753 0.4483 0.147 Uiso 1 1 calc R . .
H19C H 0.2132 1.4808 0.3617 0.147 Uiso 1 1 calc R . .


_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 1.366(4) . ?
O1 C18 1.425(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.396(4) . ?
O2 C9 1.206(3) . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
O3 C17 1.360(4) . ?
O3 C19 1.426(4) . ?
C3 C4 1.369(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.513(4) . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.501(4) . ?
C10 C11 1.516(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.505(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.378(4) . ?
C12 C17 1.406(4) . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.364(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.388(4) . ?
C16 H16A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 O1 C18 118.7(3) . . ?
O1 C1 C2 124.0(3) . . ?
O1 C1 C6 115.1(3) . . ?
C2 C1 C6 120.8(3) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C17 O3 C19 118.9(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 123.7(3) . . ?
C1 C6 C7 118.8(3) . . ?
C8 C7 C6 116.4(3) . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C7 113.5(3) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O2 C9 C10 122.1(3) . . ?
O2 C9 C8 121.8(3) . . ?
C10 C9 C8 116.1(3) . . ?
C9 C10 C11 113.1(3) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 116.5(3) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C13 C12 C17 117.6(3) . . ?
C13 C12 C11 124.6(3) . . ?
C17 C12 C11 117.8(3) . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
O3 C17 C16 124.2(3) . . ?
O3 C17 C12 115.3(3) . . ?
C16 C17 C12 120.5(3) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 4.9(5) . . . . ?
C18 O1 C1 C6 -177.0(3) . . . . ?
O1 C1 C2 C3 178.7(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C4 C5 C6 C7 -177.9(3) . . . . ?
O1 C1 C6 C5 -179.5(3) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
O1 C1 C6 C7 -0.4(4) . . . . ?
C2 C1 C6 C7 177.8(3) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C1 C6 C7 C8 -178.2(3) . . . . ?
C6 C7 C8 C9 -178.6(3) . . . . ?
C7 C8 C9 O2 0.3(5) . . . . ?
C7 C8 C9 C10 -179.0(3) . . . . ?
O2 C9 C10 C11 2.1(5) . . . . ?
C8 C9 C10 C11 -178.6(3) . . . . ?
C9 C10 C11 C12 -178.5(3) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C10 C11 C12 C17 -177.5(3) . . . . ?
C17 C12 C13 C14 0.9(5) . . . . ?
C11 C12 C13 C14 -178.5(3) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 0.9(5) . . . . ?
C19 O3 C17 C16 4.2(5) . . . . ?
C19 O3 C17 C12 -175.8(3) . . . . ?
C15 C16 C17 O3 179.4(3) . . . . ?
C15 C16 C17 C12 -0.6(5) . . . . ?
C13 C12 C17 O3 179.8(3) . . . . ?
C11 C12 C17 O3 -0.8(4) . . . . ?
C13 C12 C17 C16 -0.2(5) . . . . ?
C11 C12 C17 C16 179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
