# Electronic Supplementary Material (ESI) for Soft Matter
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Soft Matter'
_journal_coden_cambridge         0777
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Wolfgang Weissflog'
'Ute Baumeister'
'Maria-Gabriela Tamba'
'Gerhard Pelzl'
'Horst Kresse'
'Rudolf Friedemann'
'Gunther Hempel'
'Ricardo Kurz'
'Matthias Roos'
'Kurt Merzweiler'
'Antal Jakli '
'Cuiyu Zhang'
'Nicholas Diorio '
'Ralf Stannarius'
'Alexey Eremin'
'Ulrike Kornek'
_publ_contact_author_email       kurt.merzweiler@chemie.uni-halle.de
_publ_contact_author_name        'Kurt Merzweiler'

data_c:\x-step\ipds3403
_database_code_depnum_ccdc_archive 'CCDC 845881'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 O6'
_chemical_formula_weight         444.46

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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   7.4360(5)
_cell_length_b                   27.0637(18)
_cell_length_c                   10.9270(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2199.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      220(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10751
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.03
_reflns_number_total             2177
_reflns_number_gt                1522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2177
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3167(4) 0.2500 0.3801(2) 0.0424(6) Uani 1 2 d S . .
H1 H 0.345(4) 0.2500 0.292(2) 0.044(7) Uiso 1 2 d S . .
C2 C 0.2983(2) 0.29418(6) 0.44244(16) 0.0376(4) Uani 1 1 d . . .
H2 H 0.310(2) 0.3251(7) 0.3975(16) 0.042(5) Uiso 1 1 d . . .
C3 C 0.2658(2) 0.29434(5) 0.56828(14) 0.0294(4) Uani 1 1 d . . .
C4 C 0.2502(3) 0.2500 0.6350(2) 0.0274(5) Uani 1 2 d S . .
C5 C 0.2101(4) 0.2500 0.7705(2) 0.0349(5) Uani 1 2 d S . .
H3 H 0.140(3) 0.2796(7) 0.7941(17) 0.050(5) Uiso 1 1 d . . .
H4 H 0.320(5) 0.2500 0.819(3) 0.066(9) Uiso 1 2 d S . .
C6 C 0.2597(2) 0.34361(6) 0.63069(15) 0.0308(4) Uani 1 1 d . . .
C7 C 0.1854(2) 0.42828(6) 0.58623(14) 0.0293(3) Uani 1 1 d . . .
C8 C 0.0941(2) 0.44588(6) 0.68751(14) 0.0323(4) Uani 1 1 d . . .
H5 H 0.0395 0.4243 0.7422 0.039 Uiso 1 1 calc R . .
C9 C 0.0860(2) 0.49646(6) 0.70554(14) 0.0298(4) Uani 1 1 d . . .
H6 H 0.0247 0.5088 0.7731 0.036 Uiso 1 1 calc R . .
C10 C 0.1682(2) 0.52945(5) 0.62406(13) 0.0263(3) Uani 1 1 d . . .
C11 C 0.2575(2) 0.51033(6) 0.52266(13) 0.0295(4) Uani 1 1 d . . .
H7 H 0.3119 0.5317 0.4673 0.035 Uiso 1 1 calc R . .
C12 C 0.2663(2) 0.45952(6) 0.50323(15) 0.0314(4) Uani 1 1 d . . .
H8 H 0.3259 0.4469 0.4353 0.038 Uiso 1 1 calc R . .
C13 C 0.1565(2) 0.58418(6) 0.64804(14) 0.0298(3) Uani 1 1 d . . .
C14 C 0.2427(2) 0.61936(6) 0.55851(16) 0.0333(4) Uani 1 1 d . . .
H10 H 0.194(2) 0.6132(7) 0.4772(19) 0.046(5) Uiso 1 1 d . . .
H9 H 0.372(3) 0.6100(7) 0.5499(16) 0.045(5) Uiso 1 1 d . . .
C15 C 0.2237(3) 0.67326(7) 0.5937(2) 0.0482(5) Uani 1 1 d . . .
H12 H 0.293(3) 0.6802(8) 0.675(2) 0.063(6) Uiso 1 1 d . . .
H13 H 0.272(3) 0.6938(9) 0.532(2) 0.064(7) Uiso 1 1 d . . .
H11 H 0.099(4) 0.6831(8) 0.610(2) 0.070(7) Uiso 1 1 d . . .
O1 O 0.18468(15) 0.37772(4) 0.55479(10) 0.0356(3) Uani 1 1 d . . .
O2 O 0.31771(18) 0.35329(4) 0.73013(11) 0.0470(4) Uani 1 1 d . . .
O3 O 0.07874(18) 0.59919(4) 0.73931(11) 0.0455(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0641(17) 0.0311(13) 0.0322(13) 0.000 0.0026(12) 0.000
C2 0.0498(11) 0.0268(9) 0.0362(9) 0.0034(7) -0.0015(7) -0.0023(7)
C3 0.0290(8) 0.0237(8) 0.0355(8) -0.0010(6) -0.0047(6) -0.0009(6)
C4 0.0227(10) 0.0256(11) 0.0339(11) 0.000 -0.0034(9) 0.000
C5 0.0401(14) 0.0286(12) 0.0360(13) 0.000 0.0033(11) 0.000
C6 0.0317(8) 0.0247(8) 0.0360(9) 0.0016(7) -0.0043(7) -0.0020(6)
C7 0.0320(8) 0.0232(8) 0.0326(8) -0.0018(6) -0.0081(6) 0.0014(6)
C8 0.0335(8) 0.0306(9) 0.0327(8) 0.0048(7) 0.0003(7) -0.0034(7)
C9 0.0286(8) 0.0314(9) 0.0295(8) -0.0013(7) 0.0020(6) 0.0013(6)
C10 0.0263(7) 0.0259(8) 0.0267(7) -0.0012(6) -0.0037(6) 0.0018(6)
C11 0.0328(8) 0.0274(9) 0.0283(7) 0.0015(6) 0.0017(7) 0.0003(7)
C12 0.0357(8) 0.0293(8) 0.0292(8) -0.0025(7) 0.0023(7) 0.0048(6)
C13 0.0306(8) 0.0300(8) 0.0289(8) -0.0022(7) -0.0039(7) 0.0043(6)
C14 0.0386(9) 0.0273(8) 0.0342(9) -0.0004(7) -0.0036(7) 0.0009(7)
C15 0.0616(14) 0.0283(9) 0.0546(13) 0.0012(9) 0.0048(11) -0.0007(9)
O1 0.0482(7) 0.0223(6) 0.0361(6) -0.0014(5) -0.0097(5) 0.0024(5)
O2 0.0670(8) 0.0297(6) 0.0443(7) -0.0040(6) -0.0220(6) 0.0004(6)
O3 0.0621(8) 0.0331(7) 0.0414(7) -0.0042(5) 0.0135(6) 0.0069(6)

_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 C2 1.383(2) 8_565 ?
C1 C2 1.383(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.4087(19) . ?
C3 C6 1.498(2) . ?
C4 C3 1.4087(19) 8_565 ?
C4 C5 1.511(3) . ?
C6 O2 1.1981(19) . ?
C6 O1 1.3608(19) . ?
C7 C12 1.378(2) . ?
C7 C8 1.383(2) . ?
C7 O1 1.4108(19) . ?
C8 C9 1.384(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.392(2) . ?
C10 C13 1.507(2) . ?
C11 C12 1.393(2) . ?
C13 O3 1.2221(19) . ?
C13 C14 1.508(2) . ?
C14 C15 1.515(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
C2 C1 C2 119.7(2) 8_565 . ?
C1 C2 C3 120.30(17) . . ?
C2 C3 C4 121.41(15) . . ?
C2 C3 C6 117.14(14) . . ?
C4 C3 C6 121.34(15) . . ?
C3 C4 C3 116.82(19) 8_565 . ?
C3 C4 C5 121.56(10) 8_565 . ?
C3 C4 C5 121.56(10) . . ?
O2 C6 O1 123.50(14) . . ?
O2 C6 C3 126.64(14) . . ?
O1 C6 C3 109.80(13) . . ?
C12 C7 C8 121.98(14) . . ?
C12 C7 O1 115.88(13) . . ?
C8 C7 O1 121.81(14) . . ?
C7 C8 C9 118.42(14) . . ?
C8 C9 C10 121.36(14) . . ?
C11 C10 C9 118.51(14) . . ?
C11 C10 C13 122.11(14) . . ?
C9 C10 C13 119.37(13) . . ?
C10 C11 C12 120.71(14) . . ?
C7 C12 C11 119.01(14) . . ?
O3 C13 C10 119.74(14) . . ?
O3 C13 C14 121.38(14) . . ?
C10 C13 C14 118.88(13) . . ?
C13 C14 C15 113.79(15) . . ?
C6 O1 C7 120.54(12) . . ?

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
C2 C1 C2 C3 1.6(4) 8_565 . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C6 176.02(19) . . . . ?
C2 C3 C4 C3 -1.1(3) . . . 8_565 ?
C6 C3 C4 C3 -177.20(11) . . . 8_565 ?
C2 C3 C4 C5 -178.35(19) . . . . ?
C6 C3 C4 C5 5.6(3) . . . . ?
C2 C3 C6 O2 -141.57(18) . . . . ?
C4 C3 C6 O2 34.7(3) . . . . ?
C2 C3 C6 O1 35.51(19) . . . . ?
C4 C3 C6 O1 -148.26(16) . . . . ?
C12 C7 C8 C9 -0.5(2) . . . . ?
O1 C7 C8 C9 -173.58(14) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C13 -179.66(14) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C13 C10 C11 C12 179.85(14) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
O1 C7 C12 C11 174.15(13) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C11 C10 C13 O3 -178.95(15) . . . . ?
C9 C10 C13 O3 1.5(2) . . . . ?
C11 C10 C13 C14 0.6(2) . . . . ?
C9 C10 C13 C14 -178.93(14) . . . . ?
O3 C13 C14 C15 0.4(2) . . . . ?
C10 C13 C14 C15 -179.23(16) . . . . ?
O2 C6 O1 C7 5.6(2) . . . . ?
C3 C6 O1 C7 -171.62(13) . . . . ?
C12 C7 O1 C6 122.51(15) . . . . ?
C8 C7 O1 C6 -64.04(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.037

# Attachment ''