# 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. 
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data_007-14195
_database_code_depnum_ccdc_archive 'CCDC 1055302'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 O4'
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.36

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.8516(3)
_cell_length_b                   9.0800(4)
_cell_length_c                   11.1409(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.971(8)
_cell_angle_gamma                90
_cell_volume                     846.79(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10420
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      68.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.694
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            27457
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.196
_diffrn_reflns_theta_max         68.089
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3044
_reflns_number_gt                2862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.973

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_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. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.0745P] 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_abs_structure_details 
; 
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.12(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3044
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.28061(15) 0.07450(16) 0.84645(12) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.5172(2) 0.4602(2) 0.82941(18) 0.0272(4) Uani 1 1 d . . . . .
H1A H 0.5848 0.4336 0.7772 0.033 Uiso 1 1 calc R U . . .
H1B H 0.5881 0.5007 0.9107 0.033 Uiso 1 1 calc R U . . .
O2 O 0.11445(14) 0.71329(15) 0.68603(11) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.4382(2) 0.3222(2) 0.85650(17) 0.0268(4) Uani 1 1 d . . . . .
H2A H 0.5196 0.2550 0.9115 0.032 Uiso 1 1 calc R U . . .
H2B H 0.3614 0.3478 0.9009 0.032 Uiso 1 1 calc R U . . .
O3 O 0.35572(15) 0.25111(14) 0.73672(11) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.2775(2) 0.1264(2) 0.74603(17) 0.0261(4) Uani 1 1 d . . . . .
C5 C 0.1839(2) 0.0641(2) 0.61879(18) 0.0288(4) Uani 1 1 d . . . . .
H5A H 0.2241 -0.0354 0.6091 0.035 Uiso 1 1 calc R U . . .
H5B H 0.1966 0.1277 0.5505 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0062(2) 0.0554(2) 0.60826(19) 0.0295(4) Uani 1 1 d . . . . .
H6A H -0.0561 0.0120 0.5254 0.035 Uiso 1 1 calc R U . . .
H6B H -0.0063 -0.0088 0.6763 0.035 Uiso 1 1 calc R U . . .
C7 C -0.0557(2) 0.2063(2) 0.61997(18) 0.0290(4) Uani 1 1 d . . . . .
H7 H -0.0988 0.2621 0.5444 0.035 Uiso 1 1 calc R U . . .
C8 C -0.0544(2) 0.2676(2) 0.72857(18) 0.0278(4) Uani 1 1 d . . . . .
H8 H -0.0298 0.2063 0.8015 0.033 Uiso 1 1 calc R U . . .
C9 C -0.0881(2) 0.4217(2) 0.74339(19) 0.0280(4) Uani 1 1 d . . . . .
H9 H -0.1404 0.4758 0.6684 0.034 Uiso 1 1 calc R U . . .
C10 C -0.0518(2) 0.4935(2) 0.85291(19) 0.0286(4) Uani 1 1 d . . . . .
H10 H -0.0146 0.4374 0.9289 0.034 Uiso 1 1 calc R U . . .
C11 C -0.0656(2) 0.6561(2) 0.86479(19) 0.0297(4) Uani 1 1 d . . . . .
H11A H -0.1121 0.6782 0.9324 0.036 Uiso 1 1 calc R U . . .
H11B H -0.1379 0.6966 0.7840 0.036 Uiso 1 1 calc R U . . .
C12 C 0.0996(2) 0.7297(2) 0.89686(17) 0.0278(4) Uani 1 1 d . . . . .
H12A H 0.0880 0.8379 0.9000 0.033 Uiso 1 1 calc R U . . .
H12B H 0.1692 0.6961 0.9813 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1747(2) 0.6906(2) 0.79817(17) 0.0241(4) Uani 1 1 d . . . . .
O14 O 0.31719(14) 0.62303(15) 0.84900(12) 0.0256(3) Uani 1 1 d . . . . .
C15 C 0.3996(2) 0.5791(2) 0.76073(17) 0.0254(4) Uani 1 1 d . . . . .
H15 H 0.3208 0.5366 0.6825 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4820(2) 0.7099(2) 0.72527(16) 0.0248(4) Uani 1 1 d . . . . .
C17 C 0.5116(2) 0.7101(2) 0.60999(17) 0.0316(4) Uani 1 1 d . . . . .
H17 H 0.4765 0.6297 0.5531 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5918(2) 0.8264(3) 0.5775(2) 0.0352(5) Uani 1 1 d . . . . .
H18 H 0.6108 0.8256 0.4983 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6445(2) 0.9438(2) 0.6598(2) 0.0335(5) Uani 1 1 d . . . . .
H19 H 0.7004 1.0232 0.6378 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6151(2) 0.9444(2) 0.7741(2) 0.0331(5) Uani 1 1 d . . . . .
H20 H 0.6504 1.0249 0.8308 0.040 Uiso 1 1 calc R U . . .
C21 C 0.5344(2) 0.8283(2) 0.80641(18) 0.0296(4) Uani 1 1 d . . . . .
H21 H 0.5147 0.8300 0.8853 0.036 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 C4 1.206(2) . ?
C1 C2 1.512(3) . ?
C1 C15 1.522(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C13 1.206(2) . ?
C2 O3 1.448(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C4 1.349(2) . ?
C4 C5 1.501(3) . ?
C5 C6 1.541(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.496(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.329(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.452(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.327(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.491(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.540(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.500(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.350(2) . ?
O14 C15 1.458(2) . ?
C15 C16 1.512(3) . ?
C15 H15 1.0000 . ?
C16 C21 1.384(3) . ?
C16 C17 1.392(2) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 H21 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
C2 C1 C15 113.74(15) . . ?
C2 C1 H1A 108.8 . . ?
C15 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C15 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
O3 C2 C1 108.23(15) . . ?
O3 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O3 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C4 O3 C2 114.91(14) . . ?
O1 C4 O3 122.82(17) . . ?
O1 C4 C5 124.60(18) . . ?
O3 C4 C5 112.55(16) . . ?
C4 C5 C6 109.12(15) . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C5 109.87(16) . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 124.62(18) . . ?
C8 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
C7 C8 C9 124.50(19) . . ?
C7 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C10 C9 C8 125.49(19) . . ?
C10 C9 H9 117.3 . . ?
C8 C9 H9 117.3 . . ?
C9 C10 C11 124.42(19) . . ?
C9 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C12 110.59(16) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 109.92(15) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 O14 123.39(16) . . ?
O2 C13 C12 124.52(16) . . ?
O14 C13 C12 112.08(14) . . ?
C13 O14 C15 116.45(13) . . ?
O14 C15 C16 110.56(15) . . ?
O14 C15 C1 105.40(14) . . ?
C16 C15 C1 112.28(14) . . ?
O14 C15 H15 109.5 . . ?
C16 C15 H15 109.5 . . ?
C1 C15 H15 109.5 . . ?
C21 C16 C17 118.58(18) . . ?
C21 C16 C15 121.80(16) . . ?
C17 C16 C15 119.58(17) . . ?
C18 C17 C16 120.56(19) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.33(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.37(19) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.31(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.84(18) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?

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
C15 C1 C2 O3 67.67(19) . . . . ?
C1 C2 O3 C4 -179.27(14) . . . . ?
C2 O3 C4 O1 -2.8(2) . . . . ?
C2 O3 C4 C5 175.51(15) . . . . ?
O1 C4 C5 C6 57.3(2) . . . . ?
O3 C4 C5 C6 -120.94(16) . . . . ?
C4 C5 C6 C7 60.8(2) . . . . ?
C5 C6 C7 C8 -90.7(2) . . . . ?
C6 C7 C8 C9 168.72(17) . . . . ?
C7 C8 C9 C10 -163.09(19) . . . . ?
C8 C9 C10 C11 170.54(18) . . . . ?
C9 C10 C11 C12 -101.6(2) . . . . ?
C10 C11 C12 C13 56.4(2) . . . . ?
C11 C12 C13 O2 56.6(2) . . . . ?
C11 C12 C13 O14 -121.78(16) . . . . ?
O2 C13 O14 C15 1.0(2) . . . . ?
C12 C13 O14 C15 179.42(15) . . . . ?
C13 O14 C15 C16 79.09(18) . . . . ?
C13 O14 C15 C1 -159.36(15) . . . . ?
C2 C1 C15 O14 64.47(19) . . . . ?
C2 C1 C15 C16 -175.10(15) . . . . ?
O14 C15 C16 C21 27.8(2) . . . . ?
C1 C15 C16 C21 -89.6(2) . . . . ?
O14 C15 C16 C17 -154.43(15) . . . . ?
C1 C15 C16 C17 88.2(2) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
C15 C16 C17 C18 -177.77(18) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C15 C16 C21 C20 177.49(17) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030

_shelxl_version_number           2014/6

