# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1469161'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;
_audit_creation_date             2015-03-20
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_moiety         'C21 H22 O3'
_chemical_formula_weight         322.40
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2519(11)
_cell_length_b                   9.9263(12)
_cell_length_c                   18.4119(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1690.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2349
_cell_measurement_theta_min      25.60
_cell_measurement_theta_max      76.50
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            8282
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         5.062
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3021
_reflns_number_gt                2977
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0704
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     221
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0455P)²+0.2254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0260(19)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T., Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.67130(13) 0.70438(11) 0.57391(6) 0.0212(3) Uani 1 1 d . . . . .
O8 O 0.50623(12) 0.91060(12) 0.49914(6) 0.0254(3) Uani 1 1 d . . . . .
O16 O 0.86529(12) 1.04981(12) 0.47274(6) 0.0220(3) Uani 1 1 d . . . . .
C1A C 0.66020(16) 0.73483(17) 0.64675(8) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.73095(17) 0.82328(15) 0.53726(8) 0.0172(3) Uani 1 1 d . . . . .
H2 H 0.8262 0.8019 0.5144 0.021 Uiso 1 1 calc R U . . .
C3 C 0.74737(16) 0.93634(16) 0.59457(8) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.6765 1.0098 0.5839 0.020 Uiso 1 1 calc R U . . .
C3A C 0.70282(16) 0.86427(16) 0.66356(8) 0.0180(3) Uani 1 1 d . . . . .
C4 C 0.69793(17) 0.90767(17) 0.73511(8) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.7265 0.9967 0.7475 0.026 Uiso 1 1 calc R U . . .
C5 C 0.65045(18) 0.81877(18) 0.78867(8) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.6468 0.8471 0.8379 0.028 Uiso 1 1 calc R U . . .
C6 C 0.60855(18) 0.68890(18) 0.77015(8) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.5769 0.6291 0.8072 0.028 Uiso 1 1 calc R U . . .
C7 C 0.61200(18) 0.64448(17) 0.69843(9) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.5825 0.5559 0.6856 0.026 Uiso 1 1 calc R U . . .
C8 C 0.61819(17) 0.85824(15) 0.47927(8) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.63954(17) 0.81830(16) 0.40190(8) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.76145(18) 0.74955(16) 0.37747(9) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.8399 0.7336 0.4096 0.026 Uiso 1 1 calc R U . . .
C11 C 0.76840(19) 0.70423(18) 0.30607(9) 0.0264(4) Uani 1 1 d . . . . .
H11 H 0.8516 0.6574 0.2895 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6543(2) 0.72725(19) 0.25925(9) 0.0282(4) Uani 1 1 d . . . . .
H12 H 0.6583 0.6940 0.2109 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5336(2) 0.7988(2) 0.28251(9) 0.0282(4) Uani 1 1 d . . . . .
H13 H 0.4564 0.8162 0.2498 0.034 Uiso 1 1 calc R U . . .
C14 C 0.52630(18) 0.84465(18) 0.35340(9) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.4442 0.8941 0.3692 0.028 Uiso 1 1 calc R U . . .
C15 C 0.89997(17) 0.99567(16) 0.59706(8) 0.0189(3) Uani 1 1 d . . . . .
H15A H 0.9058 1.0619 0.6371 0.023 Uiso 1 1 calc R U . . .
H15B H 0.9700 0.9227 0.6074 0.023 Uiso 1 1 calc R U . . .
C16 C 0.94120(16) 1.06425(15) 0.52626(8) 0.0163(3) Uani 1 1 d . . . . .
C17 C 1.07713(16) 1.15231(15) 0.52476(8) 0.0169(3) Uani 1 1 d . . . . .
C18 C 1.04719(18) 1.28089(17) 0.56863(9) 0.0224(4) Uani 1 1 d . . . . .
H18A H 1.1311 1.3409 0.5657 0.027 Uiso 1 1 calc R U . . .
H18B H 1.0293 1.2571 0.6195 0.027 Uiso 1 1 calc R U . . .
H18C H 0.9621 1.3266 0.5487 0.027 Uiso 1 1 calc R U . . .
C19 C 1.20522(17) 1.07728(17) 0.55838(9) 0.0232(4) Uani 1 1 d . . . . .
H19A H 1.2239 0.9947 0.5307 0.028 Uiso 1 1 calc R U . . .
H19B H 1.1827 1.0541 0.6089 0.028 Uiso 1 1 calc R U . . .
H19C H 1.2911 1.1350 0.5571 0.028 Uiso 1 1 calc R U . . .
C20 C 1.11279(19) 1.18961(18) 0.44620(9) 0.0244(4) Uani 1 1 d . . . . .
H20A H 1.1275 1.1073 0.4178 0.029 Uiso 1 1 calc R U . . .
H20B H 1.2011 1.2441 0.4451 0.029 Uiso 1 1 calc R U . . .
H20C H 1.0326 1.2413 0.4254 0.029 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1A 1.3786(18) . ?
O1 C2 1.4673(18) . ?
O8 C8 1.215(2) . ?
O16 C16 1.2185(19) . ?
C1A C3A 1.379(2) . ?
C1A C7 1.382(2) . ?
C2 C8 1.533(2) . ?
C2 C3 1.548(2) . ?
C2 H2 1.0000 . ?
C3 C3A 1.515(2) . ?
C3 C15 1.530(2) . ?
C3 H3 1.0000 . ?
C3A C4 1.387(2) . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.492(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.401(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.519(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.532(2) . ?
C17 C20 1.529(2) . ?
C17 C19 1.530(2) . ?
C17 C18 1.536(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1A O1 C2 107.39(11) . . ?
O1 C1A C3A 113.66(13) . . ?
O1 C1A C7 123.48(15) . . ?
C3A C1A C7 122.86(15) . . ?
O1 C2 C8 104.27(12) . . ?
O1 C2 C3 107.86(11) . . ?
C8 C2 C3 112.18(12) . . ?
O1 C2 H2 110.8 . . ?
C8 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
C3A C3 C15 114.06(12) . . ?
C3A C3 C2 101.68(12) . . ?
C15 C3 C2 112.95(12) . . ?
C3A C3 H3 109.3 . . ?
C15 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C1A C3A C4 119.55(14) . . ?
C1A C3A C3 109.24(13) . . ?
C4 C3A C3 131.20(15) . . ?
C3A C4 C5 119.05(15) . . ?
C3A C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.13(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.35(15) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C1A C7 C6 117.06(15) . . ?
C1A C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
O8 C8 C9 120.92(14) . . ?
O8 C8 C2 117.87(14) . . ?
C9 C8 C2 120.99(13) . . ?
C10 C9 C14 119.41(15) . . ?
C10 C9 C8 123.09(14) . . ?
C14 C9 C8 117.38(14) . . ?
C11 C10 C9 120.08(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.05(17) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.37(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.82(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.22(16) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 C3 112.23(12) . . ?
C16 C15 H15A 109.2 . . ?
C3 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C3 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O16 C16 C15 119.76(13) . . ?
O16 C16 C17 121.72(14) . . ?
C15 C16 C17 118.51(13) . . ?
C20 C17 C19 109.47(13) . . ?
C20 C17 C16 109.41(12) . . ?
C19 C17 C16 110.54(12) . . ?
C20 C17 C18 109.58(13) . . ?
C19 C17 C18 109.36(13) . . ?
C16 C17 C18 108.46(12) . . ?
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 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C2 O1 C1A C3A 1.60(17) . . . . ?
C2 O1 C1A C7 -177.97(15) . . . . ?
C1A O1 C2 C8 -123.00(13) . . . . ?
C1A O1 C2 C3 -3.58(16) . . . . ?
O1 C2 C3 C3A 3.99(15) . . . . ?
C8 C2 C3 C3A 118.26(13) . . . . ?
O1 C2 C3 C15 126.65(13) . . . . ?
C8 C2 C3 C15 -119.08(14) . . . . ?
O1 C1A C3A C4 -179.57(14) . . . . ?
C7 C1A C3A C4 0.0(2) . . . . ?
O1 C1A C3A C3 1.11(18) . . . . ?
C7 C1A C3A C3 -179.32(15) . . . . ?
C15 C3 C3A C1A -125.01(14) . . . . ?
C2 C3 C3A C1A -3.11(16) . . . . ?
C15 C3 C3A C4 55.8(2) . . . . ?
C2 C3 C3A C4 177.68(16) . . . . ?
C1A C3A C4 C5 0.3(2) . . . . ?
C3 C3A C4 C5 179.44(16) . . . . ?
C3A C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
O1 C1A C7 C6 179.09(15) . . . . ?
C3A C1A C7 C6 -0.4(2) . . . . ?
C5 C6 C7 C1A 0.6(2) . . . . ?
O1 C2 C8 O8 74.42(16) . . . . ?
C3 C2 C8 O8 -42.03(19) . . . . ?
O1 C2 C8 C9 -100.27(15) . . . . ?
C3 C2 C8 C9 143.28(14) . . . . ?
O8 C8 C9 C10 -175.34(15) . . . . ?
C2 C8 C9 C10 -0.8(2) . . . . ?
O8 C8 C9 C14 0.5(2) . . . . ?
C2 C8 C9 C14 175.07(14) . . . . ?
C14 C9 C10 C11 -1.9(2) . . . . ?
C8 C9 C10 C11 173.94(15) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 2.1(2) . . . . ?
C8 C9 C14 C13 -173.92(15) . . . . ?
C3A C3 C15 C16 178.76(13) . . . . ?
C2 C3 C15 C16 63.31(16) . . . . ?
C3 C15 C16 O16 -10.9(2) . . . . ?
C3 C15 C16 C17 168.07(13) . . . . ?
O16 C16 C17 C20 -11.2(2) . . . . ?
C15 C16 C17 C20 169.79(14) . . . . ?
O16 C16 C17 C19 -131.87(15) . . . . ?
C15 C16 C17 C19 49.17(18) . . . . ?
O16 C16 C17 C18 108.25(16) . . . . ?
C15 C16 C17 C18 -70.72(17) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


