# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1478751'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H27 O'
_chemical_formula_weight         535.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.6823(14)
_cell_length_b                   14.1831(8)
_cell_length_c                   19.4393(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.9212(17)
_cell_angle_gamma                90
_cell_volume                     6388.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_F_000             2248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63194
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5781
_reflns_number_gt                4070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+5.1198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5781
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.46740(6) 0.49657(10) 0.43148(8) 0.0502(4) Uani 1 1 d . . . . .
C1 C 0.51045(10) 0.31378(18) 0.44999(13) 0.0573(6) Uani 1 1 d . . . . .
H1A H 0.5240 0.3442 0.4944 0.086 Uiso 1 1 calc R U . . .
H1B H 0.5275 0.3433 0.4148 0.086 Uiso 1 1 calc R U . . .
H1C H 0.5211 0.2484 0.4537 0.086 Uiso 1 1 calc R U . . .
C20 C 0.31633(10) 0.51204(16) 0.52792(11) 0.0498(6) Uani 1 1 d . . . . .
H20 H 0.2939 0.5639 0.5343 0.060 Uiso 1 1 calc R U . . .
C19 C 0.35166(9) 0.51696(15) 0.47887(10) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.41571(9) 0.27545(15) 0.48597(10) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.4450 0.2528 0.5257 0.053 Uiso 1 1 calc R U . . .
C2 C 0.44552(9) 0.32228(15) 0.42969(10) 0.0427(5) Uani 1 1 d . . . . .
C4 C 0.38255(9) 0.19295(14) 0.44802(11) 0.0432(5) Uani 1 1 d . . . . .
C5 C 0.35539(11) 0.12053(16) 0.47593(12) 0.0542(6) Uani 1 1 d . . . . .
H5 H 0.3537 0.1212 0.5233 0.065 Uiso 1 1 calc R U . . .
C6 C 0.33073(11) 0.04721(16) 0.43345(13) 0.0583(6) Uani 1 1 d . . . . .
H6 H 0.3124 -0.0015 0.4522 0.070 Uiso 1 1 calc R U . . .
C9 C 0.38544(9) 0.19114(14) 0.37706(10) 0.0424(5) Uani 1 1 d . . . . .
C7 C 0.33325(11) 0.04613(17) 0.36340(13) 0.0595(7) Uani 1 1 d . . . . .
H7 H 0.3162 -0.0032 0.3350 0.071 Uiso 1 1 calc R U . . .
C8 C 0.36072(11) 0.11738(16) 0.33475(12) 0.0544(6) Uani 1 1 d . . . . .
H8 H 0.3626 0.1158 0.2875 0.065 Uiso 1 1 calc R U . . .
C12 C 0.35371(10) 0.34317(16) 0.24288(10) 0.0488(6) Uani 1 1 d . . . . .
C11 C 0.38594(9) 0.34895(15) 0.31216(10) 0.0416(5) Uani 1 1 d . . . . .
C10 C 0.42018(9) 0.27312(15) 0.35781(10) 0.0419(5) Uani 1 1 d . . . . .
H10 H 0.4515 0.2500 0.3362 0.050 Uiso 1 1 calc R U . . .
C35 C 0.35307(9) 0.60253(14) 0.43605(11) 0.0429(5) Uani 1 1 d . . . . .
C13 C 0.32062(12) 0.42124(18) 0.21712(12) 0.0601(7) Uani 1 1 d . . . . .
H13 H 0.2979 0.4184 0.1720 0.072 Uiso 1 1 calc R U . . .
C14 C 0.32002(12) 0.50265(17) 0.25541(11) 0.0599(7) Uani 1 1 d . . . . .
H14 H 0.2967 0.5527 0.2361 0.072 Uiso 1 1 calc R U . . .
C34 C 0.35139(10) 0.69012(16) 0.46788(12) 0.0538(6) Uani 1 1 d . . . . .
H34 H 0.3492 0.6924 0.5151 0.065 Uiso 1 1 calc R U . . .
C33 C 0.35280(12) 0.77313(17) 0.43205(14) 0.0666(7) Uani 1 1 d . . . . .
H33 H 0.3519 0.8306 0.4548 0.080 Uiso 1 1 calc R U . . .
C32 C 0.35558(14) 0.77055(19) 0.36186(15) 0.0770(8) Uani 1 1 d . . . . .
H32 H 0.3573 0.8263 0.3372 0.092 Uiso 1 1 calc R U . . .
C31 C 0.35574(13) 0.68513(18) 0.32876(13) 0.0663(7) Uani 1 1 d . . . . .
H31 H 0.3566 0.6842 0.2812 0.080 Uiso 1 1 calc R U . . .
C30 C 0.35464(10) 0.60019(15) 0.36370(11) 0.0492(6) Uani 1 1 d . . . . .
C15 C 0.35402(10) 0.51110(15) 0.32311(11) 0.0471(5) Uani 1 1 d . . . . .
C29 C 0.40898(13) 0.22563(19) 0.18845(13) 0.0657(7) Uani 1 1 d . . . . .
H29 H 0.4428 0.2554 0.2108 0.079 Uiso 1 1 calc R U . . .
C16 C 0.38646(9) 0.43227(15) 0.34920(10) 0.0414(5) Uani 1 1 d . . . . .
C18 C 0.38425(9) 0.43645(14) 0.47302(10) 0.0381(5) Uani 1 1 d . . . . .
C17 C 0.42305(9) 0.42567(14) 0.42180(10) 0.0396(5) Uani 1 1 d . . . . .
C22 C 0.34511(10) 0.35121(16) 0.55959(10) 0.0469(5) Uani 1 1 d . . . . .
C28 C 0.41214(16) 0.1475(2) 0.14705(15) 0.0806(9) Uani 1 1 d . . . . .
H28 H 0.4479 0.1249 0.1420 0.097 Uiso 1 1 calc R U . . .
C24 C 0.35619(11) 0.26037(16) 0.19717(10) 0.0513(6) Uani 1 1 d . . . . .
C23 C 0.38019(9) 0.35348(14) 0.51002(10) 0.0404(5) Uani 1 1 d . . . . .
C27 C 0.3628(2) 0.1035(2) 0.11358(15) 0.0878(10) Uani 1 1 d . . . . .
H27 H 0.3649 0.0502 0.0864 0.105 Uiso 1 1 calc R U . . .
C25 C 0.30720(13) 0.2158(2) 0.16145(13) 0.0728(8) Uani 1 1 d . . . . .
H25 H 0.2711 0.2386 0.1653 0.087 Uiso 1 1 calc R U . . .
C26 C 0.31079(18) 0.1378(2) 0.12004(16) 0.0884(10) Uani 1 1 d . . . . .
H26 H 0.2772 0.1086 0.0964 0.106 Uiso 1 1 calc R U . . .
C21 C 0.31398(11) 0.43189(16) 0.56705(11) 0.0525(6) Uani 1 1 d . . . . .
H21 H 0.2905 0.4319 0.5999 0.063 Uiso 1 1 calc R U . . .
C41 C 0.38558(15) 0.2232(2) 0.64407(12) 0.0739(8) Uani 1 1 d . . . . .
H41 H 0.4226 0.2455 0.6446 0.089 Uiso 1 1 calc R U . . .
C39 C 0.3222(2) 0.1114(2) 0.68300(18) 0.1006(13) Uani 1 1 d . . . . .
H39 H 0.3167 0.0583 0.7089 0.121 Uiso 1 1 calc R U . . .
C37 C 0.28350(15) 0.2338(2) 0.60521(15) 0.0747(8) Uani 1 1 d . . . . .
H37 H 0.2513 0.2645 0.5794 0.090 Uiso 1 1 calc R U . . .
C36 C 0.33834(12) 0.26719(17) 0.60369(11) 0.0566(7) Uani 1 1 d . . . . .
C40 C 0.3773(2) 0.1440(2) 0.68461(15) 0.0979(12) Uani 1 1 d . . . . .
H40 H 0.4088 0.1138 0.7123 0.117 Uiso 1 1 calc R U . . .
C38 C 0.2763(2) 0.1557(2) 0.64452(19) 0.0977(11) Uani 1 1 d . . . . .
H38 H 0.2393 0.1334 0.6444 0.117 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 C17 1.438(2) . ?
C1 C2 1.511(3) . ?
C20 C21 1.375(3) . ?
C20 C19 1.394(3) . ?
C19 C18 1.396(3) . ?
C19 C35 1.476(3) . ?
C3 C4 1.514(3) . ?
C3 C23 1.521(3) . ?
C3 C2 1.567(3) . ?
C2 C17 1.557(3) . ?
C2 C10 1.566(3) . ?
C4 C5 1.381(3) . ?
C4 C9 1.395(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.375(4) . ?
C9 C8 1.384(3) . ?
C9 C10 1.515(3) . ?
C7 C8 1.380(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.407(3) . ?
C12 C24 1.481(3) . ?
C11 C16 1.383(3) . ?
C11 C10 1.518(3) . ?
C35 C34 1.392(3) . ?
C35 C30 1.415(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.399(3) . ?
C34 C33 1.372(3) . ?
C33 C32 1.380(4) . ?
C32 C31 1.372(4) . ?
C31 C30 1.386(3) . ?
C30 C15 1.488(3) . ?
C15 C16 1.392(3) . ?
C29 C28 1.380(4) . ?
C29 C24 1.386(4) . ?
C16 C17 1.499(3) . ?
C18 C23 1.393(3) . ?
C18 C17 1.496(3) . ?
C22 C21 1.385(3) . ?
C22 C23 1.397(3) . ?
C22 C36 1.496(3) . ?
C28 C27 1.366(5) . ?
C24 C25 1.376(3) . ?
C27 C26 1.354(5) . ?
C25 C26 1.381(4) . ?
C41 C36 1.376(4) . ?
C41 C40 1.409(4) . ?
C39 C38 1.341(5) . ?
C39 C40 1.379(5) . ?
C37 C38 1.376(4) . ?
C37 C36 1.389(4) . ?

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
C21 C20 C19 121.2(2) . . ?
C20 C19 C18 115.77(19) . . ?
C20 C19 C35 120.90(19) . . ?
C18 C19 C35 123.32(18) . . ?
C4 C3 C23 116.62(18) . . ?
C4 C3 C2 104.51(16) . . ?
C23 C3 C2 105.29(17) . . ?
C1 C2 C17 114.18(18) . . ?
C1 C2 C10 112.29(18) . . ?
C17 C2 C10 105.74(16) . . ?
C1 C2 C3 111.39(18) . . ?
C17 C2 C3 105.89(16) . . ?
C10 C2 C3 106.82(16) . . ?
C5 C4 C9 119.8(2) . . ?
C5 C4 C3 128.34(19) . . ?
C9 C4 C3 111.69(18) . . ?
C6 C5 C4 119.9(2) . . ?
C7 C6 C5 120.1(2) . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 C10 128.17(19) . . ?
C4 C9 C10 111.72(18) . . ?
C6 C7 C8 120.8(2) . . ?
C7 C8 C9 119.4(2) . . ?
C13 C12 C11 116.9(2) . . ?
C13 C12 C24 120.35(19) . . ?
C11 C12 C24 122.7(2) . . ?
C16 C11 C12 119.5(2) . . ?
C16 C11 C10 110.79(17) . . ?
C12 C11 C10 129.58(19) . . ?
C9 C10 C11 115.86(17) . . ?
C9 C10 C2 104.41(16) . . ?
C11 C10 C2 105.44(16) . . ?
C34 C35 C30 118.1(2) . . ?
C34 C35 C19 118.50(18) . . ?
C30 C35 C19 123.34(18) . . ?
C14 C13 C12 122.8(2) . . ?
C13 C14 C15 120.9(2) . . ?
C33 C34 C35 122.3(2) . . ?
C34 C33 C32 119.4(2) . . ?
C31 C32 C33 119.5(2) . . ?
C32 C31 C30 122.4(2) . . ?
C31 C30 C35 118.3(2) . . ?
C31 C30 C15 118.5(2) . . ?
C35 C30 C15 123.19(19) . . ?
C16 C15 C14 116.2(2) . . ?
C16 C15 C30 123.01(19) . . ?
C14 C15 C30 120.8(2) . . ?
C28 C29 C24 121.0(3) . . ?
C11 C16 C15 123.52(18) . . ?
C11 C16 C17 112.23(18) . . ?
C15 C16 C17 124.16(18) . . ?
C23 C18 C19 123.41(19) . . ?
C23 C18 C17 112.02(18) . . ?
C19 C18 C17 124.32(18) . . ?
O1 C17 C18 111.95(16) . . ?
O1 C17 C16 110.13(16) . . ?
C18 C17 C16 107.79(16) . . ?
O1 C17 C2 114.84(16) . . ?
C18 C17 C2 105.97(17) . . ?
C16 C17 C2 105.73(16) . . ?
C21 C22 C23 117.3(2) . . ?
C21 C22 C36 118.4(2) . . ?
C23 C22 C36 124.3(2) . . ?
C27 C28 C29 120.0(3) . . ?
C25 C24 C29 117.6(2) . . ?
C25 C24 C12 122.2(2) . . ?
C29 C24 C12 120.2(2) . . ?
C18 C23 C22 119.35(19) . . ?
C18 C23 C3 110.76(18) . . ?
C22 C23 C3 129.86(19) . . ?
C26 C27 C28 119.8(3) . . ?
C24 C25 C26 121.0(3) . . ?
C27 C26 C25 120.6(3) . . ?
C20 C21 C22 122.8(2) . . ?
C36 C41 C40 119.3(3) . . ?
C38 C39 C40 120.7(3) . . ?
C38 C37 C36 120.7(3) . . ?
C41 C36 C37 119.1(3) . . ?
C41 C36 C22 121.2(3) . . ?
C37 C36 C22 119.7(2) . . ?
C39 C40 C41 119.6(3) . . ?
C39 C38 C37 120.4(4) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049




