# 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_Compound2o
_database_code_depnum_ccdc_archive 'CCDC 1843923'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-12-19 downloaded from the CCDC.
;

# Dataset cdwdl23

_audit_creation_method           SHELXL-97

_publ_contact_phone              312-413-7383
_publ_contact_fax                312-996-0431
_publ_contact_email              dwink@uic.edu



_chemical_formula_sum            'C21 H24 O4'
_chemical_formula_weight         340.40

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2996(4)
_cell_length_b                   14.6723(11)
_cell_length_c                   19.1704(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1771.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9703
_cell_measurement_theta_min      2.9687
_cell_measurement_theta_max      21.7459

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  CCD
_diffrn_reflns_number            23114
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         24.79
_reflns_number_total             2927
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker)'
_computing_cell_refinement       'SAINT (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration unk
_refine_ls_abs_structure_Flack   0.6(15)
_refine_ls_number_reflns         2927
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_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
C1 C 0.6778(5) 0.2841(2) 0.93578(14) 0.0554(8) Uani 1 1 d . . .
O1 O 0.8165(3) 0.23601(16) 0.95836(11) 0.0664(6) Uani 1 1 d . . .
O2 O 0.6525(4) 0.36994(13) 0.96063(11) 0.0714(7) Uani 1 1 d . . .
C3 C 0.4735(6) 0.4137(2) 0.92857(16) 0.0723(10) Uani 1 1 d . . .
H3A H 0.5161 0.4700 0.9060 0.087 Uiso 1 1 calc R . .
H3B H 0.3651 0.4273 0.9630 0.087 Uiso 1 1 calc R . .
C4 C 0.3936(5) 0.34706(17) 0.87638(13) 0.0484(7) Uani 1 1 d . . .
C5 C 0.2275(4) 0.35720(17) 0.83056(13) 0.0480(7) Uani 1 1 d . . .
H5 H 0.1461 0.4099 0.8276 0.058 Uiso 1 1 calc R . .
C6 C 0.1936(4) 0.28193(16) 0.78961(12) 0.0369(6) Uani 1 1 d . . .
C7 C 0.0482(4) 0.24995(15) 0.73218(11) 0.0345(6) Uani 1 1 d . . .
H7 H -0.0946 0.2367 0.7498 0.041 Uiso 1 1 calc R . .
C8 C 0.0405(3) 0.30686(16) 0.66628(12) 0.0349(6) Uani 1 1 d . . .
C9 C 0.1842(4) 0.27424(16) 0.61049(12) 0.0381(6) Uani 1 1 d . . .
H9 H 0.1891 0.3124 0.5685 0.046 Uiso 1 1 calc R . .
C10 C 0.1544(4) 0.16974(16) 0.59700(11) 0.0350(6) Uani 1 1 d . . .
C11 C 0.3084(3) 0.15638(15) 0.66055(11) 0.0324(5) Uani 1 1 d . . .
H11 H 0.4076 0.1053 0.6559 0.039 Uiso 1 1 calc R . .
C12 C 0.1917(3) 0.16051(14) 0.72981(11) 0.0271(5) Uani 1 1 d . . .
O12 O 0.0904(2) 0.07634(11) 0.74074(8) 0.0368(4) Uani 1 1 d . . .
H12 H 0.0190 0.0789 0.7765 0.055 Uiso 1 1 calc R . .
C13 C 0.3145(3) 0.20186(15) 0.79222(11) 0.0303(5) Uani 1 1 d . . .
C14 C 0.4809(3) 0.18889(16) 0.83916(11) 0.0325(6) Uani 1 1 d . . .
C15 C 0.5161(4) 0.26760(17) 0.88083(12) 0.0421(7) Uani 1 1 d . . .
C16 C 0.5999(3) 0.09912(17) 0.84902(11) 0.0343(6) Uani 1 1 d . . .
O16 O 0.8249(2) 0.11360(13) 0.85476(9) 0.0462(5) Uani 1 1 d . . .
H16 H 0.8502 0.1436 0.8899 0.069 Uiso 1 1 calc R . .
C17 C 0.5162(5) 0.0540(2) 0.91521(13) 0.0533(8) Uani 1 1 d . . .
H17A H 0.5891 -0.0027 0.9226 0.080 Uiso 1 1 calc R . .
H17B H 0.3669 0.0426 0.9104 0.080 Uiso 1 1 calc R . .
H17C H 0.5401 0.0935 0.9543 0.080 Uiso 1 1 calc R . .
C18 C 0.5765(4) 0.03561(17) 0.78766(13) 0.0417(6) Uani 1 1 d . . .
H18A H 0.6345 0.0639 0.7467 0.063 Uiso 1 1 calc R . .
H18B H 0.4289 0.0226 0.7802 0.063 Uiso 1 1 calc R . .
H18C H 0.6513 -0.0201 0.7970 0.063 Uiso 1 1 calc R . .
C19 C -0.0813(5) 0.37930(18) 0.66137(16) 0.0533(7) Uani 1 1 d . . .
H19A H -0.0808 0.4139 0.6207 0.064 Uiso 1 1 calc R . .
H19B H -0.1679 0.3959 0.6985 0.064 Uiso 1 1 calc R . .
C20 C -0.0680(4) 0.13170(18) 0.59929(14) 0.0467(7) Uani 1 1 d . . .
H20A H -0.1466 0.1534 0.5597 0.070 Uiso 1 1 calc R . .
H20B H -0.1368 0.1512 0.6414 0.070 Uiso 1 1 calc R . .
H20C H -0.0622 0.0663 0.5982 0.070 Uiso 1 1 calc R . .
C21 C 0.2596(5) 0.14024(19) 0.52912(12) 0.0554(8) Uani 1 1 d . . .
H21A H 0.2494 0.0752 0.5244 0.083 Uiso 1 1 calc R . .
H21B H 0.4064 0.1579 0.5297 0.083 Uiso 1 1 calc R . .
H21C H 0.1894 0.1690 0.4905 0.083 Uiso 1 1 calc R . .
C22 C 0.4029(4) 0.25069(17) 0.64280(13) 0.0402(6) Uani 1 1 d . . .
H22A H 0.5184 0.2488 0.6094 0.048 Uiso 1 1 calc R . .
H22B H 0.4397 0.2871 0.6833 0.048 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
C1 O1 1.204(4) . ?
C1 O2 1.356(4) . ?
C1 C15 1.485(4) . ?
O2 C3 1.436(4) . ?
C3 C4 1.487(4) . ?
C4 C5 1.374(4) . ?
C4 C15 1.401(4) . ?
C5 C6 1.372(3) . ?
C6 C13 1.401(3) . ?
C6 C7 1.507(3) . ?
C7 C8 1.515(3) . ?
C7 C12 1.594(3) . ?
C8 C19 1.314(3) . ?
C8 C9 1.481(3) . ?
C9 C22 1.550(3) . ?
C9 C10 1.566(3) . ?
C10 C20 1.509(4) . ?
C10 C21 1.523(3) . ?
C10 C11 1.569(3) . ?
C11 C12 1.519(3) . ?
C11 C22 1.544(3) . ?
C12 O12 1.406(3) . ?
C12 C13 1.549(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.422(3) . ?
C14 C16 1.527(3) . ?
C16 O16 1.438(3) . ?
C16 C18 1.508(3) . ?
C16 C17 1.525(3) . ?

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 O2 120.2(3) . . ?
O1 C1 C15 131.1(3) . . ?
O2 C1 C15 108.6(3) . . ?
C1 O2 C3 110.9(2) . . ?
O2 C3 C4 105.0(2) . . ?
C5 C4 C15 123.3(2) . . ?
C5 C4 C3 128.1(3) . . ?
C15 C4 C3 108.7(3) . . ?
C6 C5 C4 113.4(2) . . ?
C5 C6 C13 124.8(2) . . ?
C5 C6 C7 139.7(2) . . ?
C13 C6 C7 95.48(18) . . ?
C6 C7 C8 117.19(19) . . ?
C6 C7 C12 86.12(16) . . ?
C8 C7 C12 116.61(17) . . ?
C19 C8 C9 124.5(2) . . ?
C19 C8 C7 121.6(2) . . ?
C9 C8 C7 113.88(19) . . ?
C8 C9 C22 109.1(2) . . ?
C8 C9 C10 111.26(19) . . ?
C22 C9 C10 87.37(18) . . ?
C20 C10 C21 108.9(2) . . ?
C20 C10 C9 117.9(2) . . ?
C21 C10 C9 111.6(2) . . ?
C20 C10 C11 120.3(2) . . ?
C21 C10 C11 111.03(19) . . ?
C9 C10 C11 85.43(17) . . ?
C12 C11 C22 110.09(18) . . ?
C12 C11 C10 112.00(17) . . ?
C22 C11 C10 87.43(17) . . ?
O12 C12 C11 108.36(17) . . ?
O12 C12 C13 117.12(17) . . ?
C11 C12 C13 116.70(16) . . ?
O12 C12 C7 117.49(16) . . ?
C11 C12 C7 109.40(17) . . ?
C13 C12 C7 86.49(15) . . ?
C14 C13 C6 123.1(2) . . ?
C14 C13 C12 145.1(2) . . ?
C6 C13 C12 91.69(17) . . ?
C13 C14 C15 111.6(2) . . ?
C13 C14 C16 124.5(2) . . ?
C15 C14 C16 123.7(2) . . ?
C4 C15 C14 123.8(2) . . ?
C4 C15 C1 106.6(2) . . ?
C14 C15 C1 129.6(3) . . ?
O16 C16 C18 104.30(19) . . ?
O16 C16 C17 109.94(19) . . ?
C18 C16 C17 110.3(2) . . ?
O16 C16 C14 111.5(2) . . ?
C18 C16 C14 112.88(18) . . ?
C17 C16 C14 107.96(19) . . ?
C11 C22 C9 86.86(17) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        24.79
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
