# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_7juna_0m
_database_code_depnum_ccdc_archive 'CCDC 1406195'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H36 O4'
_chemical_formula_weight         676.77

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           Monoclinic
_symmetry_space_group_name_H-M   Cc
_symmetry_space_group_name_HALL  'C -2yc'
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   18.012(2)
_cell_length_b                   6.5373(8)
_cell_length_c                   14.3077(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.302(4)
_cell_angle_gamma                90.00
_cell_volume                     1667.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1646
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      24.24

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6737
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.1087
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3191
_reflns_number_gt                2112
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1688P)²+6.5699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(6)
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.3025
_refine_ls_wR_factor_gt          0.2589
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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 0.5133(4) 0.7859(11) 0.7710(5) 0.0208(15) Uani 1 1 d . . .
C2 C 0.4936(3) 0.5792(9) 0.7496(4) 0.0067(7) Uani 1 1 d . . .
H2 H 0.4611 0.4993 0.7791 0.008 Uiso 1 1 calc R . .
C3 C 0.5308(3) 0.5192(9) 0.6781(4) 0.0067(7) Uani 1 1 d . . .
C4 C 0.5250(4) 0.3330(11) 0.6339(6) 0.0297(18) Uani 1 1 d . . .
H4 H 0.4953 0.2302 0.6539 0.036 Uiso 1 1 calc R . .
C5 C 0.5637(4) 0.3004(10) 0.5599(5) 0.0236(16) Uani 1 1 d . . .
H5 H 0.5619 0.1736 0.5303 0.028 Uiso 1 1 calc R . .
C6 C 0.6058(4) 0.4585(12) 0.5293(6) 0.0304(19) Uani 1 1 d . . .
C7 C 0.6665(4) 0.6879(11) 0.4493(5) 0.0257(17) Uani 1 1 d . . .
C8 C 0.6499(3) 0.7853(9) 0.5290(4) 0.0067(7) Uani 1 1 d . . .
H8 H 0.6613 0.9195 0.5472 0.008 Uiso 1 1 calc R . .
C9 C 0.6127(4) 0.6432(11) 0.5764(5) 0.0258(18) Uani 1 1 d . . .
C10 C 0.5761(4) 0.6814(10) 0.6544(5) 0.0235(16) Uani 1 1 d . . .
C11 C 0.4767(4) 0.8802(11) 0.8422(5) 0.0233(16) Uani 1 1 d . . .
C12 C 0.4949(4) 1.0819(11) 0.8691(5) 0.0229(16) Uani 1 1 d . . .
H12 H 0.5311 1.1517 0.8414 0.027 Uiso 1 1 calc R . .
C13 C 0.4596(4) 1.1782(12) 0.9362(5) 0.0282(18) Uani 1 1 d . . .
H13 H 0.4712 1.3139 0.9515 0.034 Uiso 1 1 calc R . .
C14 C 0.4071(4) 1.0768(12) 0.9814(5) 0.0279(18) Uani 1 1 d . . .
C15 C 0.3873(4) 0.8749(12) 0.9535(5) 0.0288(19) Uani 1 1 d . . .
H15 H 0.3516 0.8046 0.9819 0.035 Uiso 1 1 calc R . .
C16 C 0.4213(4) 0.7813(12) 0.8834(5) 0.0271(18) Uani 1 1 d . . .
H16 H 0.4067 0.6499 0.8637 0.033 Uiso 1 1 calc R . .
C17 C 0.3708(5) 1.1770(13) 1.0583(6) 0.035(2) Uani 1 1 d . . .
H17A H 0.3196 1.1332 1.0536 0.053 Uiso 1 1 calc R . .
H17B H 0.3725 1.3230 1.0513 0.053 Uiso 1 1 calc R . .
H17C H 0.3974 1.1387 1.1188 0.053 Uiso 1 1 calc R . .
C18 C 0.7024(4) 0.8120(13) 0.3862(5) 0.0286(18) Uani 1 1 d . . .
C19 C 0.7115(4) 0.7412(11) 0.2956(5) 0.0254(17) Uani 1 1 d . . .
H19 H 0.6943 0.6115 0.2765 0.030 Uiso 1 1 calc R . .
C20 C 0.7460(4) 0.8631(12) 0.2337(6) 0.0293(18) Uani 1 1 d . . .
H20 H 0.7507 0.8130 0.1740 0.035 Uiso 1 1 calc R . .
C21 C 0.7730(4) 1.0546(13) 0.2590(5) 0.030(2) Uani 1 1 d . . .
C22 C 0.7621(4) 1.1292(11) 0.3479(5) 0.0282(17) Uani 1 1 d . . .
H22 H 0.7780 1.2605 0.3661 0.034 Uiso 1 1 calc R . .
C23 C 0.7272(4) 1.0072(11) 0.4097(6) 0.0287(18) Uani 1 1 d . . .
H23 H 0.7207 1.0599 0.4683 0.034 Uiso 1 1 calc R . .
C24 C 0.8097(5) 1.1867(14) 0.1932(6) 0.038(2) Uani 1 1 d . . .
H24A H 0.7909 1.1511 0.1291 0.057 Uiso 1 1 calc R . .
H24B H 0.8630 1.1657 0.2045 0.057 Uiso 1 1 calc R . .
H24C H 0.7988 1.3277 0.2039 0.057 Uiso 1 1 calc R . .
O1 O 0.5649(4) 0.8460(11) 0.7155(5) 0.062(2) Uani 1 1 d . . .
O2 O 0.6422(4) 0.4857(13) 0.4446(5) 0.070(2) Uani 1 1 d . . .


_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 1.365(11) . ?
C1 C2 1.420(9) . ?
C1 C11 1.430(10) . ?
C2 C3 1.359(8) . ?
C3 C4 1.369(9) . ?
C3 C10 1.410(9) . ?
C4 C5 1.364(11) . ?
C5 C6 1.389(10) . ?
C6 C9 1.380(11) . ?
C6 O2 1.470(11) . ?
C7 C8 1.376(10) . ?
C7 O2 1.392(11) . ?
C7 C18 1.435(10) . ?
C8 C9 1.380(10) . ?
C9 C10 1.397(10) . ?
C10 O1 1.419(10) . ?
C11 C16 1.390(9) . ?
C11 C12 1.399(10) . ?
C12 C13 1.378(11) . ?
C13 C14 1.389(10) . ?
C14 C15 1.410(11) . ?
C14 C17 1.508(11) . ?
C15 C16 1.391(10) . ?
C18 C23 1.378(11) . ?
C18 C19 1.407(10) . ?
C19 C20 1.402(11) . ?
C20 C21 1.372(11) . ?
C21 C22 1.402(11) . ?
C21 C24 1.500(11) . ?
C22 C23 1.404(11) . ?

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 108.6(6) . . ?
O1 C1 C11 135.5(6) . . ?
C2 C1 C11 116.0(6) . . ?
C3 C2 C1 107.6(5) . . ?
C2 C3 C4 126.3(6) . . ?
C2 C3 C10 109.3(5) . . ?
C4 C3 C10 124.4(6) . . ?
C5 C4 C3 119.0(7) . . ?
C4 C5 C6 119.4(7) . . ?
C9 C6 C5 120.8(7) . . ?
C9 C6 O2 106.1(7) . . ?
C5 C6 O2 132.8(8) . . ?
C8 C7 O2 112.0(7) . . ?
C8 C7 C18 115.6(6) . . ?
O2 C7 C18 132.4(7) . . ?
C7 C8 C9 106.0(6) . . ?
C8 C9 C6 111.4(7) . . ?
C8 C9 C10 126.2(7) . . ?
C6 C9 C10 121.8(7) . . ?
C9 C10 C3 114.5(6) . . ?
C9 C10 O1 138.8(7) . . ?
C3 C10 O1 106.4(6) . . ?
C16 C11 C12 118.4(7) . . ?
C16 C11 C1 122.3(6) . . ?
C12 C11 C1 119.2(6) . . ?
C13 C12 C11 120.6(7) . . ?
C12 C13 C14 121.3(7) . . ?
C13 C14 C15 118.5(7) . . ?
C13 C14 C17 121.9(7) . . ?
C15 C14 C17 119.6(7) . . ?
C16 C15 C14 119.7(7) . . ?
C11 C16 C15 121.3(7) . . ?
C23 C18 C19 116.9(7) . . ?
C23 C18 C7 122.0(7) . . ?
C19 C18 C7 121.1(7) . . ?
C20 C19 C18 121.1(7) . . ?
C21 C20 C19 121.6(7) . . ?
C20 C21 C22 117.8(7) . . ?
C20 C21 C24 122.1(8) . . ?
C22 C21 C24 120.1(8) . . ?
C21 C22 C23 120.5(7) . . ?
C18 C23 C22 122.1(7) . . ?
C1 O1 C10 108.1(6) . . ?
C7 O2 C6 104.5(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.134
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
