# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ay65
_database_code_depnum_ccdc_archive 'CCDC 1048635'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O2'
_chemical_formula_weight         280.35

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                   8.6637(7)
_cell_length_b                   15.5478(12)
_cell_length_c                   11.0472(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1488.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3809
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(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  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13621
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             2626
_reflns_number_gt                2542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL-2014/7

_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)+(0.0414P)²+0.2675P] 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 
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_restrained_S_all      1.263
_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
C1 C 0.7721(3) 0.00001(19) 0.3123(3) 0.0380(7) Uani 1 1 d . . . . .
H1 H 0.7983 0.0176 0.2296 0.046 Uiso 1 1 calc R U . . .
C2 C 0.7652(4) -0.1404(2) 0.2351(5) 0.0629(11) Uani 1 1 d . . . . .
H2A H 0.7895 -0.1170 0.1559 0.075 Uiso 1 1 calc R U . . .
H2B H 0.6998 -0.1904 0.2236 0.075 Uiso 1 1 calc R U . . .
C3 C 0.9126(4) -0.1672(2) 0.2976(5) 0.0624(11) Uani 1 1 d . . . . .
H3A H 0.8873 -0.1983 0.3711 0.075 Uiso 1 1 calc R U . . .
H3B H 0.9699 -0.2057 0.2451 0.075 Uiso 1 1 calc R U . . .
C4 C 1.0124(4) -0.0909(2) 0.3290(3) 0.0439(8) Uani 1 1 d . . . . .
C5 C 1.1531(4) -0.1092(3) 0.4094(4) 0.0628(11) Uani 1 1 d . . . . .
H5A H 1.1268 -0.1055 0.4946 0.075 Uiso 1 1 calc R U . . .
H5B H 1.1962 -0.1656 0.3927 0.075 Uiso 1 1 calc R U . . .
C6 C 1.2647(4) -0.0376(3) 0.3726(5) 0.0683(12) Uani 1 1 d . . . . .
H6A H 1.2959 -0.0031 0.4415 0.082 Uiso 1 1 calc R U . . .
H6B H 1.3557 -0.0603 0.3326 0.082 Uiso 1 1 calc R U . . .
C7 C 1.1649(4) 0.0129(2) 0.2863(4) 0.0594(10) Uani 1 1 d . . . . .
H7 H 1.2237 0.0506 0.2322 0.071 Uiso 1 1 calc R U . . .
C8 C 1.0382(4) 0.0593(2) 0.3552(4) 0.0571(10) Uani 1 1 d . . . . .
H8A H 0.9921 0.1045 0.3066 0.068 Uiso 1 1 calc R U . . .
H8B H 1.0770 0.0838 0.4300 0.068 Uiso 1 1 calc R U . . .
C9 C 0.9229(4) -0.0136(2) 0.3799(3) 0.0399(7) Uani 1 1 d . . . . .
H9 H 0.9046 -0.0203 0.4669 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6672(3) 0.0685(2) 0.3645(3) 0.0386(8) Uani 1 1 d . . . . .
C11 C 0.6729(4) 0.0902(2) 0.4843(3) 0.0521(9) Uani 1 1 d . . . . .
H11 H 0.7430 0.0622 0.5343 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5766(5) 0.1533(3) 0.5341(4) 0.0651(11) Uani 1 1 d . . . . .
H12 H 0.5833 0.1661 0.6162 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4743(5) 0.1956(3) 0.4641(4) 0.0629(11) Uani 1 1 d . . . . .
H13 H 0.4112 0.2375 0.4982 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4622(4) 0.1767(2) 0.3395(3) 0.0478(9) Uani 1 1 d . . . . .
C15 C 0.3577(5) 0.2207(2) 0.2643(4) 0.0620(11) Uani 1 1 d . . . . .
H15 H 0.2944 0.2628 0.2976 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3472(5) 0.2033(3) 0.1447(5) 0.0689(12) Uani 1 1 d . . . . .
H16 H 0.2783 0.2338 0.0964 0.083 Uiso 1 1 calc R U . . .
C17 C 0.4403(5) 0.1392(3) 0.0937(4) 0.0622(11) Uani 1 1 d . . . . .
H17 H 0.4330 0.1271 0.0114 0.075 Uiso 1 1 calc R U . . .
C18 C 0.5414(4) 0.0946(2) 0.1638(3) 0.0499(9) Uani 1 1 d . . . . .
H18 H 0.6009 0.0516 0.1287 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5586(4) 0.1119(2) 0.2887(3) 0.0398(8) Uani 1 1 d . . . . .
O1 O 0.6843(3) -0.07766(14) 0.3038(3) 0.0513(6) Uani 1 1 d . . . . .
O2 O 1.0819(3) -0.05380(17) 0.2238(2) 0.0543(6) Uani 1 1 d . . . . .


_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
C1 O1 1.430(4) . ?
C1 C10 1.514(4) . ?
C1 C9 1.520(4) . ?
C1 H1 0.9800 . ?
C2 O1 1.420(5) . ?
C2 C3 1.511(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.430(4) . ?
C4 C5 1.536(5) . ?
C4 C9 1.536(4) . ?
C5 C6 1.531(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.507(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O2 1.438(5) . ?
C7 C8 1.518(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.535(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C10 C11 1.367(5) . ?
C10 C19 1.429(5) . ?
C11 C12 1.399(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.348(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.411(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(5) . ?
C14 C19 1.425(4) . ?
C15 C16 1.352(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.413(5) . ?
C18 H18 0.9300 . ?

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
O1 C1 C10 107.5(2) . . ?
O1 C1 C9 111.8(3) . . ?
C10 C1 C9 115.3(3) . . ?
O1 C1 H1 107.3 . . ?
C10 C1 H1 107.3 . . ?
C9 C1 H1 107.3 . . ?
O1 C2 C3 111.2(3) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C3 111.8(3) . . ?
O2 C4 C5 102.2(3) . . ?
C3 C4 C5 116.2(3) . . ?
O2 C4 C9 101.2(2) . . ?
C3 C4 C9 114.2(3) . . ?
C5 C4 C9 109.5(3) . . ?
C6 C5 C4 102.3(3) . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 C5 100.6(3) . . ?
C7 C6 H6A 111.6 . . ?
C5 C6 H6A 111.6 . . ?
C7 C6 H6B 111.6 . . ?
C5 C6 H6B 111.6 . . ?
H6A C6 H6B 109.4 . . ?
O2 C7 C6 102.4(3) . . ?
O2 C7 C8 102.9(3) . . ?
C6 C7 C8 110.2(4) . . ?
O2 C7 H7 113.5 . . ?
C6 C7 H7 113.5 . . ?
C8 C7 H7 113.5 . . ?
C7 C8 C9 102.0(3) . . ?
C7 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
C7 C8 H8B 111.4 . . ?
C9 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
C1 C9 C8 111.7(3) . . ?
C1 C9 C4 111.3(3) . . ?
C8 C9 C4 100.6(3) . . ?
C1 C9 H9 110.9 . . ?
C8 C9 H9 110.9 . . ?
C4 C9 H9 110.9 . . ?
C11 C10 C19 118.4(3) . . ?
C11 C10 C1 121.4(3) . . ?
C19 C10 C1 120.3(3) . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 C19 119.2(3) . . ?
C13 C14 C19 119.2(3) . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.8(4) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 117.2(3) . . ?
C18 C19 C10 123.5(3) . . ?
C14 C19 C10 119.3(3) . . ?
C2 O1 C1 110.7(3) . . ?
C4 O2 C7 96.4(3) . . ?

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
O1 C2 C3 C4 -53.5(5) . . . . ?
C2 C3 C4 O2 -72.1(4) . . . . ?
C2 C3 C4 C5 171.2(4) . . . . ?
C2 C3 C4 C9 42.1(5) . . . . ?
O2 C4 C5 C6 30.8(4) . . . . ?
C3 C4 C5 C6 152.8(4) . . . . ?
C9 C4 C5 C6 -75.9(4) . . . . ?
C4 C5 C6 C7 4.4(4) . . . . ?
C5 C6 C7 O2 -38.4(4) . . . . ?
C5 C6 C7 C8 70.5(4) . . . . ?
O2 C7 C8 C9 30.8(4) . . . . ?
C6 C7 C8 C9 -77.8(3) . . . . ?
O1 C1 C9 C8 162.0(3) . . . . ?
C10 C1 C9 C8 -74.8(4) . . . . ?
O1 C1 C9 C4 50.4(4) . . . . ?
C10 C1 C9 C4 173.6(3) . . . . ?
C7 C8 C9 C1 -113.6(3) . . . . ?
C7 C8 C9 C4 4.5(4) . . . . ?
O2 C4 C9 C1 79.7(3) . . . . ?
C3 C4 C9 C1 -40.6(4) . . . . ?
C5 C4 C9 C1 -173.0(3) . . . . ?
O2 C4 C9 C8 -38.8(3) . . . . ?
C3 C4 C9 C8 -159.1(3) . . . . ?
C5 C4 C9 C8 68.6(4) . . . . ?
O1 C1 C10 C11 99.6(4) . . . . ?
C9 C1 C10 C11 -25.9(4) . . . . ?
O1 C1 C10 C19 -80.1(4) . . . . ?
C9 C1 C10 C19 154.5(3) . . . . ?
C19 C10 C11 C12 -0.2(5) . . . . ?
C1 C10 C11 C12 -179.9(3) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C15 -179.2(4) . . . . ?
C12 C13 C14 C19 0.5(6) . . . . ?
C13 C14 C15 C16 179.3(4) . . . . ?
C19 C14 C15 C16 -0.4(6) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 -1.2(6) . . . . ?
C17 C18 C19 C14 1.7(5) . . . . ?
C17 C18 C19 C10 -177.8(3) . . . . ?
C15 C14 C19 C18 -0.9(4) . . . . ?
C13 C14 C19 C18 179.4(3) . . . . ?
C15 C14 C19 C10 178.6(3) . . . . ?
C13 C14 C19 C10 -1.1(4) . . . . ?
C11 C10 C19 C18 -179.6(3) . . . . ?
C1 C10 C19 C18 0.0(5) . . . . ?
C11 C10 C19 C14 1.0(4) . . . . ?
C1 C10 C19 C14 -179.4(3) . . . . ?
C3 C2 O1 C1 64.6(4) . . . . ?
C10 C1 O1 C2 169.1(3) . . . . ?
C9 C1 O1 C2 -63.4(4) . . . . ?
C3 C4 O2 C7 -179.5(3) . . . . ?
C5 C4 O2 C7 -54.5(3) . . . . ?
C9 C4 O2 C7 58.5(3) . . . . ?
C6 C7 O2 C4 58.6(3) . . . . ?
C8 C7 O2 C4 -55.8(3) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032

