# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_602103_3695_02_0m
_database_code_depnum_ccdc_archive 'CCDC 1881998'
_audit_update_record             
;
2018-11-29 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C35 H30 O5'
_chemical_formula_sum            'C35 H30 O5'
_chemical_formula_weight         530.59
_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'
_chemical_absolute_configuration rm
loop_
_space_group_symop_operation_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'
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_diffrn_ambient_temperature      273.15
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'

_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.
;

_cell_length_a                   11.3620(4)
_cell_length_b                   15.3627(7)
_cell_length_c                   16.0741(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2805.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5067
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      41.422
_cell_measurement_theta_min      5.880
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0620 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20316
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.080
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_min         2.195
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3915
_reflns_number_total             4982
_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       'SAINT V8.30C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1461 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0945
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C1'(H1'), C9(H9), C1"(H1")
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7"'(H7"'), C4(H4), C5(H5), C3"'(H3"'), C6(H6), C6"'(H6"'), C4"'(H4"'),
 C8"(H8"), C3(H3), C5"'(H5"'), C8(H8), C4"(H4"), C1(H1), C6"(H6"), C7(H7),
 C5"(H5"), C7"(H7"), C2(H2)
2.d Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C2"(H2"A,H2"B,H2"C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.064
;
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 0.41302(15) 0.66802(12) 0.63947(11) 0.0506(5) Uani 1 1 d . . . . .
O4 O 0.56817(16) 0.83957(12) 0.66320(11) 0.0523(5) Uani 1 1 d . . . . .
O3 O 0.58520(18) 0.93311(13) 0.76903(12) 0.0597(5) Uani 1 1 d . . . . .
O1 O 0.60403(16) 0.63931(13) 0.65646(13) 0.0670(6) Uani 1 1 d . . . . .
O5 O 0.35765(17) 0.82431(14) 0.76766(17) 0.0746(7) Uani 1 1 d . . . . .
C2' C 0.5137(2) 0.67013(18) 0.68179(18) 0.0474(7) Uani 1 1 d . . . . .
C2"' C 0.2741(2) 0.69087(17) 0.80534(15) 0.0398(6) Uani 1 1 d . . . . .
C10A C 0.8038(2) 0.81039(17) 0.81671(17) 0.0430(6) Uani 1 1 d . . . . .
C3' C 0.5789(2) 0.86008(18) 0.74387(16) 0.0439(6) Uani 1 1 d . . . . .
C11 C 0.5915(2) 0.77752(16) 0.79547(15) 0.0409(6) Uani 1 1 d . . . . .
C1"' C 0.3727(2) 0.74766(19) 0.77857(17) 0.0467(6) Uani 1 1 d . . . . .
C7"' C 0.1686(2) 0.7309(2) 0.82737(16) 0.0496(7) Uani 1 1 d . . . . .
H7"' H 0.161685 0.791150 0.824225 0.059 Uiso 1 1 calc R . . . .
C10 C 0.72123(19) 0.74220(17) 0.78239(16) 0.0417(6) Uani 1 1 d . . . . .
H10 H 0.737533 0.729549 0.723751 0.050 Uiso 1 1 calc R . . . .
C8A C 0.7898(2) 0.82615(18) 0.90153(17) 0.0482(7) Uani 1 1 d . . . . .
C1' C 0.4974(2) 0.70955(17) 0.76812(17) 0.0416(6) Uani 1 1 d . . . . .
H1' H 0.503171 0.661139 0.807609 0.050 Uiso 1 1 calc R . . . .
C4A C 0.7332(2) 0.66214(17) 0.83607(17) 0.0452(7) Uani 1 1 d . . . . .
C4 C 0.7561(2) 0.57785(19) 0.8096(2) 0.0562(8) Uani 1 1 d . . . . .
H4 H 0.765421 0.565986 0.753268 0.067 Uiso 1 1 calc R . . . .
C5 C 0.8894(2) 0.85465(18) 0.77247(19) 0.0522(7) Uani 1 1 d . . . . .
H5 H 0.898204 0.845272 0.715653 0.063 Uiso 1 1 calc R . . . .
C9A C 0.7177(2) 0.67933(19) 0.92067(19) 0.0525(7) Uani 1 1 d . . . . .
C3"' C 0.2817(2) 0.60133(19) 0.80859(17) 0.0517(7) Uani 1 1 d . . . . .
H3"' H 0.351311 0.573846 0.793306 0.062 Uiso 1 1 calc R . . . .
C12 C 0.5776(2) 0.79734(19) 0.88980(16) 0.0497(7) Uani 1 1 d . . . . .
H12A H 0.560531 0.858691 0.897368 0.060 Uiso 1 1 calc R . . . .
H12B H 0.512057 0.764216 0.911932 0.060 Uiso 1 1 calc R . . . .
C3" C 0.4407(2) 0.68929(19) 0.49171(17) 0.0513(7) Uani 1 1 d . . . . .
C9 C 0.6914(2) 0.77358(19) 0.93807(17) 0.0548(8) Uani 1 1 d . . . . .
H9 H 0.682702 0.784482 0.997830 0.066 Uiso 1 1 calc R . . . .
C6 C 0.9621(3) 0.9134(2) 0.8138(2) 0.0662(9) Uani 1 1 d . . . . .
H6 H 1.019628 0.943393 0.784323 0.079 Uiso 1 1 calc R . . . .
C6"' C 0.0742(2) 0.6816(3) 0.85385(19) 0.0631(8) Uani 1 1 d . . . . .
H6"' H 0.004281 0.708549 0.869308 0.076 Uiso 1 1 calc R . . . .
C4"' C 0.1869(3) 0.5523(2) 0.8343(2) 0.0651(9) Uani 1 1 d . . . . .
H4"' H 0.192498 0.491921 0.836154 0.078 Uiso 1 1 calc R . . . .
C1" C 0.4162(2) 0.62329(19) 0.55874(18) 0.0566(7) Uani 1 1 d . . . . .
H1" H 0.479742 0.580145 0.559327 0.068 Uiso 1 1 calc R . . . .
C8" C 0.5459(3) 0.6868(2) 0.4489(2) 0.0649(9) Uani 1 1 d . . . . .
H8" H 0.600189 0.643302 0.460821 0.078 Uiso 1 1 calc R . . . .
C3 C 0.7651(3) 0.5119(2) 0.8672(3) 0.0715(10) Uani 1 1 d . . . . .
H3 H 0.780474 0.455358 0.849598 0.086 Uiso 1 1 calc R . . . .
C4' C 0.5421(3) 0.9101(2) 0.60693(19) 0.0682(9) Uani 1 1 d . . . . .
H4'A H 0.527533 0.887219 0.552325 0.102 Uiso 1 1 calc GR . . . .
H4'B H 0.607760 0.949374 0.604927 0.102 Uiso 1 1 calc GR . . . .
H4'C H 0.473585 0.940722 0.626100 0.102 Uiso 1 1 calc GR . . . .
C5"' C 0.0839(3) 0.5930(3) 0.8573(2) 0.0697(9) Uani 1 1 d . . . . .
H5"' H 0.020259 0.559920 0.875285 0.084 Uiso 1 1 calc R . . . .
C8 C 0.8635(3) 0.8839(2) 0.9414(2) 0.0648(9) Uani 1 1 d . . . . .
H8 H 0.855214 0.893635 0.998223 0.078 Uiso 1 1 calc R . . . .
C4" C 0.3626(3) 0.7540(2) 0.47246(19) 0.0649(9) Uani 1 1 d . . . . .
H4" H 0.290792 0.756481 0.500149 0.078 Uiso 1 1 calc R . . . .
C1 C 0.7276(3) 0.6132(2) 0.9780(2) 0.0735(10) Uani 1 1 d . . . . .
H1 H 0.718390 0.624544 1.034422 0.088 Uiso 1 1 calc R . . . .
C6" C 0.4932(4) 0.8124(3) 0.3714(2) 0.0786(11) Uani 1 1 d . . . . .
H6" H 0.511010 0.854145 0.331453 0.094 Uiso 1 1 calc R . . . .
C7 C 0.9495(3) 0.9272(2) 0.8971(3) 0.0725(10) Uani 1 1 d . . . . .
H7 H 0.999219 0.966000 0.924269 0.087 Uiso 1 1 calc R . . . .
C5" C 0.3882(4) 0.8157(2) 0.4128(2) 0.0766(10) Uani 1 1 d . . . . .
H5" H 0.334191 0.859425 0.400768 0.092 Uiso 1 1 calc R . . . .
C7" C 0.5719(3) 0.7479(3) 0.3887(2) 0.0810(10) Uani 1 1 d . . . . .
H7" H 0.642877 0.744991 0.359955 0.097 Uiso 1 1 calc R . . . .
C2" C 0.2992(3) 0.5765(2) 0.5523(2) 0.0843(11) Uani 1 1 d . . . . .
H2"A H 0.288631 0.539742 0.600008 0.126 Uiso 1 1 calc GR . . . .
H2"B H 0.298045 0.541585 0.502723 0.126 Uiso 1 1 calc GR . . . .
H2"C H 0.236630 0.618437 0.549969 0.126 Uiso 1 1 calc GR . . . .
C2 C 0.7516(3) 0.5290(2) 0.9504(3) 0.0839(12) Uani 1 1 d . . . . .
H2 H 0.758489 0.484027 0.988856 0.101 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 C2' 1.331(3) . ?
O2 C1" 1.469(3) . ?
O4 C3' 1.340(3) . ?
O4 C4' 1.442(3) . ?
O3 C3' 1.195(3) . ?
O1 C2' 1.201(3) . ?
O5 C1"' 1.203(3) . ?
C2' C1' 1.525(4) . ?
C2"' C1"' 1.484(4) . ?
C2"' C7"' 1.393(3) . ?
C2"' C3"' 1.379(4) . ?
C10A C10 1.511(4) . ?
C10A C8A 1.394(4) . ?
C10A C5 1.383(4) . ?
C3' C11 1.522(4) . ?
C11 C10 1.584(3) . ?
C11 C1' 1.558(4) . ?
C11 C12 1.555(4) . ?
C1"' C1' 1.542(3) . ?
C7"' C6"' 1.380(4) . ?
C10 C4A 1.509(4) . ?
C8A C9 1.499(4) . ?
C8A C8 1.378(4) . ?
C4A C4 1.388(4) . ?
C4A C9A 1.396(4) . ?
C4 C3 1.376(4) . ?
C5 C6 1.392(4) . ?
C9A C9 1.505(4) . ?
C9A C1 1.376(4) . ?
C3"' C4"' 1.377(4) . ?
C12 C9 1.551(4) . ?
C3" C1" 1.506(4) . ?
C3" C8" 1.379(4) . ?
C3" C4" 1.369(4) . ?
C6 C7 1.364(5) . ?
C6"' C5"' 1.366(5) . ?
C4"' C5"' 1.378(5) . ?
C1" C2" 1.516(4) . ?
C8" C7" 1.380(5) . ?
C3 C2 1.372(5) . ?
C8 C7 1.381(5) . ?
C4" C5" 1.379(5) . ?
C1 C2 1.394(5) . ?
C6" C5" 1.367(5) . ?
C6" C7" 1.363(5) . ?

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' O2 C1" 116.2(2) . . ?
C3' O4 C4' 116.7(2) . . ?
O2 C2' C1' 111.7(2) . . ?
O1 C2' O2 123.5(3) . . ?
O1 C2' C1' 124.7(2) . . ?
C7"' C2"' C1"' 117.6(2) . . ?
C3"' C2"' C1"' 123.4(2) . . ?
C3"' C2"' C7"' 119.0(2) . . ?
C8A C10A C10 114.0(2) . . ?
C5 C10A C10 126.1(3) . . ?
C5 C10A C8A 119.9(3) . . ?
O4 C3' C11 109.9(2) . . ?
O3 C3' O4 123.6(2) . . ?
O3 C3' C11 126.3(2) . . ?
C3' C11 C10 107.50(19) . . ?
C3' C11 C1' 109.9(2) . . ?
C3' C11 C12 111.0(2) . . ?
C1' C11 C10 111.82(19) . . ?
C12 C11 C10 106.9(2) . . ?
C12 C11 C1' 109.7(2) . . ?
O5 C1"' C2"' 120.7(2) . . ?
O5 C1"' C1' 119.1(2) . . ?
C2"' C1"' C1' 120.1(2) . . ?
C6"' C7"' C2"' 120.3(3) . . ?
C10A C10 C11 107.0(2) . . ?
C4A C10 C10A 107.5(2) . . ?
C4A C10 C11 106.67(19) . . ?
C10A C8A C9 112.0(2) . . ?
C8 C8A C10A 119.8(3) . . ?
C8 C8A C9 128.1(3) . . ?
C2' C1' C11 116.0(2) . . ?
C2' C1' C1"' 111.2(2) . . ?
C1"' C1' C11 110.2(2) . . ?
C4 C4A C10 127.1(3) . . ?
C4 C4A C9A 119.9(3) . . ?
C9A C4A C10 113.1(2) . . ?
C3 C4 C4A 119.7(3) . . ?
C10A C5 C6 119.4(3) . . ?
C4A C9A C9 112.8(2) . . ?
C1 C9A C4A 120.1(3) . . ?
C1 C9A C9 127.0(3) . . ?
C4"' C3"' C2"' 120.5(3) . . ?
C9 C12 C11 110.9(2) . . ?
C8" C3" C1" 119.9(3) . . ?
C4" C3" C1" 122.1(3) . . ?
C4" C3" C8" 118.0(3) . . ?
C8A C9 C9A 107.3(2) . . ?
C8A C9 C12 107.4(2) . . ?
C9A C9 C12 107.4(2) . . ?
C7 C6 C5 120.5(3) . . ?
C5"' C6"' C7"' 119.8(3) . . ?
C3"' C4"' C5"' 119.7(3) . . ?
O2 C1" C3" 108.8(2) . . ?
O2 C1" C2" 105.1(2) . . ?
C3" C1" C2" 115.7(3) . . ?
C3" C8" C7" 121.2(3) . . ?
C2 C3 C4 120.4(3) . . ?
C6"' C5"' C4"' 120.6(3) . . ?
C8A C8 C7 120.0(3) . . ?
C3" C4" C5" 121.3(3) . . ?
C9A C1 C2 119.3(3) . . ?
C7" C6" C5" 120.0(3) . . ?
C6 C7 C8 120.4(3) . . ?
C6" C5" C4" 119.8(3) . . ?
C6" C7" C8" 119.7(3) . . ?
C3 C2 C1 120.6(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'

