# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 1563788'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2017-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.1(C23 H30 O5)'
_chemical_formula_sum            'C23 H30 O5'
_chemical_formula_weight         386.49
_chemical_absolute_configuration s
_chemical_melting_point          ?
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'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.88250(10)
_cell_length_b                   13.45840(10)
_cell_length_c                   13.64720(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1998.78(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12137
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1760
_cell_measurement_theta_min      4.0290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13682
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.257
_diffrn_reflns_theta_min         4.614
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3616
_reflns_number_total             3657
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0710
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C18(H18A,H18B), C20(H20A,H20B), C27(H27A,H27B),
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O -0.16667(11) -0.61783(8) -0.37578(8) 0.0211(3) Uani 1 1 d . . . . .
O3 O -0.03050(12) -0.85359(9) -0.59984(9) 0.0268(3) Uani 1 1 d . . . . .
H2 H -0.0134 -0.9129 -0.6027 0.040 Uiso 1 1 calc GR . . . .
O1 O -0.47241(12) -0.44850(9) -0.39474(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H -0.5094 -0.4193 -0.3511 0.041 Uiso 1 1 calc GR . . . .
O5 O -0.35700(12) -0.88459(9) -0.25089(9) 0.0276(3) Uani 1 1 d . . . . .
O4 O -0.32785(13) -1.03259(9) -0.32320(10) 0.0308(3) Uani 1 1 d . . . . .
C11 C -0.05635(16) -0.64349(12) -0.52779(13) 0.0219(4) Uani 1 1 d . . . . .
H6A H -0.0950 -0.6270 -0.5898 0.026 Uiso 1 1 calc R . . . .
H6B H 0.0317 -0.6486 -0.5374 0.026 Uiso 1 1 calc R . . . .
C2aa C -0.17267(16) -0.71479(12) -0.40233(12) 0.0184(3) Uani 1 1 d . . . . .
C3aa C -0.10004(16) -0.83622(13) -0.51912(12) 0.0200(3) Uani 1 1 d . . . . .
C4aa C -0.10782(15) -0.73778(12) -0.48638(12) 0.0191(3) Uani 1 1 d . . . . .
C0aa C -0.23004(15) -0.88290(12) -0.38628(12) 0.0192(3) Uani 1 1 d . . . . .
C1aa C -0.30602(16) -0.94538(13) -0.32183(12) 0.0222(3) Uani 1 1 d . . . . .
C1 C -0.28653(15) -0.51461(12) -0.53199(12) 0.0213(3) Uani 1 1 d . . . . .
H12A H -0.2672 -0.5474 -0.5934 0.026 Uiso 1 1 calc R . . . .
H12B H -0.3227 -0.5637 -0.4886 0.026 Uiso 1 1 calc R . . . .
C14 C -0.25847(17) -0.23867(12) -0.46854(14) 0.0265(4) Uani 1 1 d . . . . .
H13A H -0.1856 -0.2109 -0.4398 0.040 Uiso 1 1 calc GR . . . .
H13B H -0.3226 -0.1897 -0.4686 0.040 Uiso 1 1 calc GR . . . .
H13C H -0.2414 -0.2588 -0.5346 0.040 Uiso 1 1 calc GR . . . .
C4 C -0.29987(16) -0.32961(11) -0.40836(12) 0.0197(3) Uani 1 1 d . . . . .
C5 C -0.19884(16) -0.41022(11) -0.39416(12) 0.0183(3) Uani 1 1 d . . . . .
H15 H -0.2335 -0.4568 -0.3464 0.022 Uiso 1 1 calc R . . . .
C8 C 0.02834(17) -0.53212(13) -0.39223(13) 0.0251(4) Uani 1 1 d . . . . .
H16 H 0.0828 -0.4993 -0.4394 0.030 Uiso 1 1 calc R . . . .
C15 C -0.09223(16) -0.42095(13) -0.56539(13) 0.0233(4) Uani 1 1 d . . . . .
H17A H -0.0605 -0.4684 -0.6114 0.035 Uiso 1 1 calc GR . . . .
H17B H -0.0253 -0.3857 -0.5355 0.035 Uiso 1 1 calc GR . . . .
H17C H -0.1446 -0.3748 -0.5990 0.035 Uiso 1 1 calc GR . . . .
C2 C -0.38027(16) -0.43259(14) -0.55120(13) 0.0248(4) Uani 1 1 d . . . . .
H18A H -0.3470 -0.3862 -0.5987 0.030 Uiso 1 1 calc R . . . .
H18B H -0.4542 -0.4616 -0.5788 0.030 Uiso 1 1 calc R . . . .
C10 C -0.16655(15) -0.47549(11) -0.48562(11) 0.0177(3) Uani 1 1 d . . . . .
C20 C -0.31754(18) -0.78225(13) -0.26378(13) 0.0257(4) Uani 1 1 d . . . . .
H20A H -0.2728 -0.7589 -0.2068 0.031 Uiso 1 1 calc R . . . .
H20B H -0.3873 -0.7389 -0.2752 0.031 Uiso 1 1 calc R . . . .
C21 C -0.16269(15) -0.91057(12) -0.46870(13) 0.0210(3) Uani 1 1 d . . . . .
H21 H -0.1597 -0.9764 -0.4893 0.025 Uiso 1 1 calc R . . . .
C22 C -0.23640(16) -0.78646(12) -0.35140(12) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.09909(19) -0.61968(15) -0.34764(16) 0.0335(4) Uani 1 1 d . . . . .
H23A H 0.0482 -0.6527 -0.3003 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.1721 -0.5955 -0.3161 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.1213 -0.6656 -0.3985 0.050 Uiso 1 1 calc GR . . . .
C3 C -0.41285(15) -0.37691(13) -0.45782(13) 0.0224(4) Uani 1 1 d . . . . .
H24 H -0.4718 -0.3243 -0.4739 0.027 Uiso 1 1 calc R . . . .
C13 C -0.34004(18) -0.28975(13) -0.30773(13) 0.0265(4) Uani 1 1 d . . . . .
H25A H -0.2759 -0.2491 -0.2808 0.040 Uiso 1 1 calc GR . . . .
H25B H -0.3560 -0.3445 -0.2644 0.040 Uiso 1 1 calc GR . . . .
H25C H -0.4134 -0.2508 -0.3151 0.040 Uiso 1 1 calc GR . . . .
C9 C -0.08788(15) -0.56471(12) -0.44766(11) 0.0190(3) Uani 1 1 d . . . . .
C7 C -0.00126(18) -0.45688(14) -0.31138(14) 0.0307(4) Uani 1 1 d . . . . .
H27A H -0.0430 -0.4910 -0.2583 0.037 Uiso 1 1 calc R . . . .
H27B H 0.0751 -0.4305 -0.2856 0.037 Uiso 1 1 calc R . . . .
C6 C -0.08121(17) -0.37091(13) -0.34587(14) 0.0263(4) Uani 1 1 d . . . . .
H28A H -0.0358 -0.3308 -0.3925 0.032 Uiso 1 1 calc R . . . .
H28B H -0.1025 -0.3292 -0.2904 0.032 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
O2 C2aa 1.3558(19) . ?
O2 C9 1.4861(18) . ?
O3 C3aa 1.357(2) . ?
O1 C3 1.446(2) . ?
O5 C1aa 1.384(2) . ?
O5 C20 1.453(2) . ?
O4 C1aa 1.198(2) . ?
C11 C4aa 1.498(2) . ?
C11 C9 1.561(2) . ?
C2aa C4aa 1.382(2) . ?
C2aa C22 1.376(2) . ?
C3aa C4aa 1.401(2) . ?
C3aa C21 1.393(2) . ?
C0aa C1aa 1.471(2) . ?
C0aa C21 1.393(2) . ?
C0aa C22 1.384(2) . ?
C1 C2 1.526(2) . ?
C1 C10 1.544(2) . ?
C14 C4 1.541(2) . ?
C4 C5 1.557(2) . ?
C4 C3 1.540(2) . ?
C4 C13 1.538(2) . ?
C5 C10 1.566(2) . ?
C5 C6 1.534(2) . ?
C8 C12 1.534(2) . ?
C8 C9 1.538(2) . ?
C8 C7 1.532(2) . ?
C15 C10 1.542(2) . ?
C2 C3 1.520(2) . ?
C10 C9 1.563(2) . ?
C20 C22 1.487(2) . ?
C7 C6 1.522(2) . ?

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
C2aa O2 C9 108.32(12) . . ?
C1aa O5 C20 110.93(13) . . ?
C4aa C11 C9 103.23(13) . . ?
O2 C2aa C4aa 114.38(14) . . ?
O2 C2aa C22 124.32(14) . . ?
C22 C2aa C4aa 121.30(15) . . ?
O3 C3aa C4aa 117.11(15) . . ?
O3 C3aa C21 123.39(15) . . ?
C21 C3aa C4aa 119.50(15) . . ?
C2aa C4aa C11 108.33(14) . . ?
C2aa C4aa C3aa 120.49(15) . . ?
C3aa C4aa C11 131.18(15) . . ?
C21 C0aa C1aa 128.73(15) . . ?
C22 C0aa C1aa 107.59(15) . . ?
C22 C0aa C21 123.68(15) . . ?
O5 C1aa C0aa 107.80(14) . . ?
O4 C1aa O5 120.72(16) . . ?
O4 C1aa C0aa 131.47(17) . . ?
C2 C1 C10 112.91(13) . . ?
C14 C4 C5 114.41(14) . . ?
C3 C4 C14 109.15(14) . . ?
C3 C4 C5 109.29(13) . . ?
C13 C4 C14 106.38(13) . . ?
C13 C4 C5 109.43(14) . . ?
C13 C4 C3 107.98(14) . . ?
C4 C5 C10 116.75(13) . . ?
C6 C5 C4 113.74(13) . . ?
C6 C5 C10 110.40(14) . . ?
C12 C8 C9 112.89(15) . . ?
C7 C8 C12 109.12(15) . . ?
C7 C8 C9 111.71(15) . . ?
C3 C2 C1 111.63(14) . . ?
C1 C10 C5 109.16(13) . . ?
C1 C10 C9 109.70(13) . . ?
C15 C10 C1 108.46(13) . . ?
C15 C10 C5 114.42(13) . . ?
C15 C10 C9 108.20(13) . . ?
C9 C10 C5 106.84(12) . . ?
O5 C20 C22 103.69(13) . . ?
C3aa C21 C0aa 117.67(14) . . ?
C2aa C22 C0aa 117.27(15) . . ?
C2aa C22 C20 132.71(15) . . ?
C0aa C22 C20 109.99(14) . . ?
O1 C3 C4 111.87(14) . . ?
O1 C3 C2 105.97(14) . . ?
C2 C3 C4 112.64(13) . . ?
O2 C9 C11 105.21(12) . . ?
O2 C9 C8 106.68(13) . . ?
O2 C9 C10 105.80(12) . . ?
C11 C9 C10 114.20(13) . . ?
C8 C9 C11 110.95(14) . . ?
C8 C9 C10 113.23(13) . . ?
C6 C7 C8 113.57(15) . . ?
C7 C6 C5 110.35(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
