# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_tetra-mono
_database_code_depnum_ccdc_archive 'CCDC 1556103'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_audit_creation_date             04/29/2014
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        1a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H22 O'
_chemical_formula_weight         410.48

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                   19.134(10)
_cell_length_b                   10.392(4)
_cell_length_c                   10.998(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.116(10)
_cell_angle_gamma                90
_cell_volume                     2164.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    168
_cell_measurement_theta_min      1.48
_cell_measurement_theta_max      26.21

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Bruker SADABS'
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10582
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2125
_reflns_number_gt                1305
_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.
 
 _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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+1.3874P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2125
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.011
_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
C1 C 0.5000 0.1369(3) 0.7500 0.0457(8) Uani 1 2 d S T P . .
C2 C 0.44980(11) 0.2216(2) 0.8063(2) 0.0443(6) Uani 1 1 d . . . . .
C3 C 0.47063(11) 0.3439(2) 0.7884(2) 0.0426(6) Uani 1 1 d . . . . .
C4 C 0.44692(11) 0.4660(2) 0.8343(2) 0.0455(6) Uani 1 1 d . . . . .
C5 C 0.47408(11) 0.5822(2) 0.7935(2) 0.0481(6) Uani 1 1 d . . . . .
C6 C 0.45016(14) 0.6977(2) 0.8394(3) 0.0633(7) Uani 1 1 d . . . . .
H6 H 0.4659 0.7755 0.8114 0.076 Uiso 1 1 calc R U . . .
C7 C 0.40449(15) 0.6988(2) 0.9241(3) 0.0717(8) Uani 1 1 d . . . . .
H7 H 0.3896 0.7769 0.9528 0.086 Uiso 1 1 calc R U . . .
C8 C 0.38028(14) 0.5850(3) 0.9673(3) 0.0671(8) Uani 1 1 d . . . . .
H8 H 0.3502 0.5859 1.0267 0.081 Uiso 1 1 calc R U . . .
C9 C 0.40111(13) 0.4700(2) 0.9217(3) 0.0581(7) Uani 1 1 d . . . . .
H9 H 0.3841 0.3934 0.9499 0.070 Uiso 1 1 calc R U . . .
C10 C 0.39362(12) 0.1678(2) 0.8713(2) 0.0470(6) Uani 1 1 d . . . . .
C11 C 0.32237(12) 0.1793(2) 0.8255(2) 0.0533(7) Uani 1 1 d . . . . .
C12 C 0.27313(14) 0.1271(3) 0.8933(3) 0.0670(8) Uani 1 1 d . . . . .
H12 H 0.2254 0.1329 0.8628 0.080 Uiso 1 1 calc R U . . .
C13 C 0.29317(15) 0.0676(3) 1.0033(3) 0.0759(9) Uani 1 1 d . . . . .
H13 H 0.2591 0.0355 1.0478 0.091 Uiso 1 1 calc R U . . .
C14 C 0.36351(15) 0.0549(3) 1.0483(3) 0.0710(8) Uani 1 1 d . . . . .
H14 H 0.3774 0.0139 1.1230 0.085 Uiso 1 1 calc R U . . .
C15 C 0.41309(13) 0.1032(2) 0.9821(3) 0.0584(7) Uani 1 1 d . . . . .
H15 H 0.4607 0.0927 1.0117 0.070 Uiso 1 1 calc R U . . .
O1 O 0.5000 0.0199(2) 0.7500 0.0587(7) Uani 1 2 d S T P . .
C16 C 0.29792(14) 0.2490(3) 0.7088(3) 0.0742(8) Uani 1 1 d . . . . .
H16A H 0.2485 0.2332 0.6845 0.111 Uiso 1 1 calc R U . . .
H16B H 0.3239 0.2191 0.6458 0.111 Uiso 1 1 calc R U . . .
H16C H 0.3056 0.3397 0.7210 0.111 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
C1 O1 1.216(4) . ?
C1 C2 1.499(3) . ?
C1 C2 1.500(3) 2_656 ?
C2 C3 1.354(3) . ?
C2 C10 1.482(3) . ?
C3 C4 1.461(3) . ?
C3 C3 1.499(4) 2_656 ?
C4 C9 1.390(3) . ?
C4 C5 1.412(3) . ?
C5 C6 1.404(3) . ?
C5 C5 1.473(5) 2_656 ?
C6 C7 1.364(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.390(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.491(4) . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 C2 125.94(13) . . ?
O1 C1 C2 125.94(12) . 2_656 ?
C2 C1 C2 108.1(2) . 2_656 ?
C3 C2 C10 132.3(2) . . ?
C3 C2 C1 105.77(19) . . ?
C10 C2 C1 121.90(19) . . ?
C2 C3 C4 130.7(2) . . ?
C2 C3 C3 109.97(13) . 2_656 ?
C4 C3 C3 119.27(12) . 2_656 ?
C9 C4 C5 119.3(2) . . ?
C9 C4 C3 121.5(2) . . ?
C5 C4 C3 119.1(2) . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 C5 121.17(14) . 2_656 ?
C4 C5 C5 121.22(13) . 2_656 ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 121.5(2) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C11 C10 C15 119.0(2) . . ?
C11 C10 C2 122.3(2) . . ?
C15 C10 C2 118.7(2) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 C16 121.7(2) . . ?
C12 C11 C16 119.8(2) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 C1 C2 C3 177.93(12) . . . . ?
C2 C1 C2 C3 -2.07(12) 2_656 . . . ?
O1 C1 C2 C10 0.8(2) . . . . ?
C2 C1 C2 C10 -179.2(2) 2_656 . . . ?
C10 C2 C3 C4 4.2(4) . . . . ?
C1 C2 C3 C4 -172.5(2) . . . . ?
C10 C2 C3 C3 -178.1(2) . . . 2_656 ?
C1 C2 C3 C3 5.1(3) . . . 2_656 ?
C2 C3 C4 C9 8.1(4) . . . . ?
C3 C3 C4 C9 -169.4(3) 2_656 . . . ?
C2 C3 C4 C5 -175.2(2) . . . . ?
C3 C3 C4 C5 7.4(4) 2_656 . . . ?
C9 C4 C5 C6 -3.2(3) . . . . ?
C3 C4 C5 C6 180.0(2) . . . . ?
C9 C4 C5 C5 176.4(3) . . . 2_656 ?
C3 C4 C5 C5 -0.4(4) . . . 2_656 ?
C4 C5 C6 C7 2.5(4) . . . . ?
C5 C5 C6 C7 -177.1(3) 2_656 . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C6 C7 C8 C9 -1.8(4) . . . . ?
C7 C8 C9 C4 1.0(4) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
C3 C4 C9 C8 178.2(2) . . . . ?
C3 C2 C10 C11 71.5(4) . . . . ?
C1 C2 C10 C11 -112.2(2) . . . . ?
C3 C2 C10 C15 -108.7(3) . . . . ?
C1 C2 C10 C15 67.6(3) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C2 C10 C11 C12 -179.3(2) . . . . ?
C15 C10 C11 C16 178.9(2) . . . . ?
C2 C10 C11 C16 -1.3(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C16 C11 C12 C13 -177.0(3) . . . . ?
C11 C12 C13 C14 -1.7(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C10 1.6(4) . . . . ?
C11 C10 C15 C14 -2.2(4) . . . . ?
C2 C10 C15 C14 178.0(2) . . . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
