# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Qian Miao'
_publ_contact_author_email       MIAOQIAN@CUHK.EDU.HK

_publ_section_title              
;
Transistors from a Conjugated Macrocycle Molecule:
Field and Photo Effects
;
loop_
_publ_author_name
'Qian Miao.'
'Hoi-Shan Chan.'
'KaYuen Lo.'
'Qin Tang.'
'Jianbin Xu.'
'Wei Zhao.'



# Attachment 'CBDEA-OC6.cif'

data_CBDEA-OC6
_database_code_depnum_ccdc_archive 'CCDC 689532'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
'Cyclic Bis(1,8-diethynyl-9-hexyloxy-anthracene)'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H40 O2'
_chemical_formula_weight         648.80

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9279(8)
_cell_length_b                   10.0248(9)
_cell_length_c                   11.7180(10)
_cell_angle_alpha                75.067(2)
_cell_angle_beta                 67.838(2)
_cell_angle_gamma                69.165(2)
_cell_volume                     898.48(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEXII CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7913
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3059
_reflns_number_gt                1736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEXII CCD DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER APEXII CCD DIFFRACTOMETER'
_computing_data_reduction        'BRUKER APEXII CCD DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_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^)+(0.1828P)^2^+0.9951P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3059
_refine_ls_number_parameters     236
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.1102
_refine_ls_wR_factor_ref         0.3683
_refine_ls_wR_factor_gt          0.3108
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_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
O1 O -0.1128(6) 0.5364(5) 0.6915(6) 0.125(2) Uani 1 1 d D . .
C1 C -0.7776(12) 0.8482(11) 0.4608(9) 0.161(4) Uani 1 1 d . . .
H1A H -0.8509 0.9450 0.4559 0.242 Uiso 1 1 calc R . .
H1B H -0.8441 0.7822 0.5020 0.242 Uiso 1 1 calc R . .
H1C H -0.7104 0.8260 0.3783 0.242 Uiso 1 1 calc R . .
C2 C -0.6669(12) 0.8349(12) 0.5308(9) 0.158(4) Uani 1 1 d . . .
H2A H -0.6032 0.9042 0.4896 0.189 Uiso 1 1 calc R . .
H2B H -0.7364 0.8603 0.6130 0.189 Uiso 1 1 calc R . .
C3 C -0.5503(10) 0.6944(9) 0.5445(7) 0.120(3) Uani 1 1 d . . .
H3A H -0.4836 0.6677 0.4623 0.144 Uiso 1 1 calc R . .
H3B H -0.6143 0.6257 0.5883 0.144 Uiso 1 1 calc R . .
C4 C -0.4281(10) 0.6808(10) 0.6149(7) 0.119(3) Uani 1 1 d . A .
H4A H -0.3470 0.7334 0.5641 0.143 Uiso 1 1 calc R . .
H4B H -0.4913 0.7220 0.6917 0.143 Uiso 1 1 calc R . .
C5 C -0.3373(12) 0.5253(11) 0.6435(9) 0.147(3) Uani 1 1 d DU . .
C6 C -0.1511(19) 0.522(3) 0.5918(13) 0.129(12) Uani 0.277(17) 1 d PDU A 1
C6' C -0.2628(10) 0.5083(11) 0.7509(6) 0.093(4) Uani 0.723(17) 1 d PD A 2
C7 C -0.0112(6) 0.5223(6) 0.7608(5) 0.0744(15) Uani 1 1 d . . .
C8 C -0.0209(6) 0.6464(5) 0.7994(4) 0.0631(13) Uani 1 1 d . . .
C9 C -0.1449(7) 0.7807(7) 0.7820(5) 0.0802(17) Uani 1 1 d . A .
H9A H -0.2214 0.7868 0.7433 0.096 Uiso 1 1 calc R . .
C10 C -0.1517(7) 0.8983(6) 0.8213(5) 0.0775(16) Uani 1 1 d . . .
H10A H -0.2345 0.9843 0.8109 0.093 Uiso 1 1 calc R A .
C11 C -0.0367(6) 0.8933(5) 0.8772(4) 0.0659(13) Uani 1 1 d . A .
H11A H -0.0433 0.9765 0.9025 0.079 Uiso 1 1 calc R . .
C12 C 0.0865(5) 0.7678(5) 0.8958(4) 0.0538(11) Uani 1 1 d . . .
C13 C 0.0951(5) 0.6383(5) 0.8591(4) 0.0497(11) Uani 1 1 d . A .
C14 C 0.2157(5) 0.5080(5) 0.8777(4) 0.0509(11) Uani 1 1 d . . .
H14 H 0.2922 0.5038 0.9157 0.061 Uiso 1 1 calc R A .
C15 C 0.2068(6) 0.7660(5) 0.9486(4) 0.0547(11) Uani 1 1 d . A .
C16 C 0.3121(6) 0.7648(4) 0.9901(4) 0.0554(12) Uani 1 1 d . . .
C17 C 0.4295(6) 0.7625(4) 1.0402(4) 0.0560(12) Uani 1 1 d . A .
C18 C 0.5323(6) 0.7602(4) 1.0845(4) 0.0560(12) Uani 1 1 d . . .
C19 C 0.6514(6) 0.7520(5) 1.1405(4) 0.0561(12) Uani 1 1 d . A .
C20 C 0.6492(7) 0.8731(6) 1.1778(5) 0.0703(14) Uani 1 1 d . . .
H20A H 0.5710 0.9610 1.1639 0.084 Uiso 1 1 calc R A .
C21 C 0.7638(8) 0.8643(7) 1.2364(6) 0.0872(18) Uani 1 1 d . A .
H21A H 0.7600 0.9468 1.2610 0.105 Uiso 1 1 calc R . .
C22 C 0.8799(8) 0.7386(7) 1.2580(6) 0.0891(19) Uani 1 1 d . . .
H22A H 0.9530 0.7355 1.2985 0.107 Uiso 1 1 calc R A .
C23 C 0.8911(6) 0.6106(6) 1.2189(5) 0.0653(13) Uani 1 1 d . . .
C24 C 0.7767(5) 0.6160(5) 1.1599(4) 0.0517(11) 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
O1 0.092(3) 0.122(4) 0.199(5) -0.078(4) -0.090(4) 0.011(3)
C1 0.125(7) 0.164(9) 0.142(8) 0.000(7) -0.052(6) 0.013(6)
C2 0.124(7) 0.163(9) 0.138(7) -0.041(7) -0.032(6) 0.018(6)
C3 0.121(6) 0.126(6) 0.112(6) -0.025(5) -0.049(5) -0.016(5)
C4 0.115(6) 0.151(8) 0.111(5) -0.027(5) -0.053(5) -0.036(5)
C5 0.149(6) 0.149(6) 0.202(7) -0.001(5) -0.133(6) -0.047(5)
C6 0.136(14) 0.105(14) 0.100(14) -0.005(9) 0.007(9) -0.035(9)
C6' 0.086(6) 0.133(8) 0.067(5) 0.002(5) -0.017(4) -0.058(6)
C7 0.055(3) 0.099(4) 0.086(4) -0.038(3) -0.036(3) -0.010(3)
C8 0.050(3) 0.076(3) 0.065(3) -0.024(2) -0.024(2) -0.004(2)
C9 0.063(3) 0.096(4) 0.087(4) -0.035(3) -0.040(3) 0.003(3)
C10 0.068(3) 0.077(4) 0.083(4) -0.029(3) -0.037(3) 0.011(3)
C11 0.065(3) 0.061(3) 0.069(3) -0.021(2) -0.024(2) -0.004(2)
C12 0.051(2) 0.054(3) 0.054(3) -0.011(2) -0.016(2) -0.009(2)
C13 0.044(2) 0.059(3) 0.043(2) -0.0084(19) -0.0117(18) -0.013(2)
C14 0.051(2) 0.057(3) 0.048(2) -0.0113(19) -0.0162(19) -0.016(2)
C15 0.058(3) 0.047(3) 0.058(3) -0.013(2) -0.018(2) -0.010(2)
C16 0.055(3) 0.044(3) 0.066(3) -0.014(2) -0.019(2) -0.0090(19)
C17 0.057(3) 0.041(2) 0.069(3) -0.013(2) -0.022(2) -0.0076(19)
C18 0.058(3) 0.042(2) 0.069(3) -0.012(2) -0.023(2) -0.010(2)
C19 0.055(3) 0.052(3) 0.065(3) -0.015(2) -0.017(2) -0.017(2)
C20 0.068(3) 0.060(3) 0.094(4) -0.024(3) -0.027(3) -0.020(2)
C21 0.082(4) 0.078(4) 0.119(5) -0.045(3) -0.030(3) -0.024(3)
C22 0.077(4) 0.093(4) 0.124(5) -0.050(4) -0.046(4) -0.016(3)
C23 0.059(3) 0.076(3) 0.070(3) -0.031(3) -0.020(2) -0.015(2)
C24 0.047(2) 0.060(3) 0.054(2) -0.016(2) -0.0143(19) -0.019(2)

_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 C6' 1.350(7) . ?
O1 C7 1.381(6) . ?
O1 C6 1.390(10) . ?
C1 C2 1.459(12) . ?
C2 C3 1.436(12) . ?
C3 C4 1.551(9) . ?
C4 C5 1.496(12) . ?
C5 C6 1.530(10) . ?
C5 C6' 1.581(8) . ?
C7 C8 1.395(7) . ?
C7 C23 1.412(7) 2_667 ?
C8 C13 1.423(6) . ?
C8 C9 1.431(7) . ?
C9 C10 1.347(7) . ?
C10 C11 1.393(7) . ?
C11 C12 1.377(6) . ?
C12 C15 1.420(6) . ?
C12 C13 1.438(6) . ?
C13 C14 1.394(6) . ?
C14 C24 1.394(6) 2_667 ?
C15 C16 1.206(6) . ?
C16 C17 1.373(6) . ?
C17 C18 1.204(6) . ?
C18 C19 1.415(6) . ?
C19 C20 1.384(6) . ?
C19 C24 1.453(6) . ?
C20 C21 1.400(7) . ?
C21 C22 1.353(8) . ?
C22 C23 1.430(7) . ?
C23 C7 1.412(7) 2_667 ?
C23 C24 1.413(6) . ?
C24 C14 1.394(6) 2_667 ?

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
C6' O1 C7 118.5(6) . . ?
C6' O1 C6 79.3(7) . . ?
C7 O1 C6 156.6(9) . . ?
C3 C2 C1 114.9(10) . . ?
C2 C3 C4 115.2(8) . . ?
C5 C4 C3 109.5(6) . . ?
C4 C5 C6 103.4(13) . . ?
C4 C5 C6' 108.6(7) . . ?
C6 C5 C6' 68.3(6) . . ?
O1 C6 C5 105.3(9) . . ?
O1 C6' C5 104.6(6) . . ?
O1 C7 C8 117.5(5) . . ?
O1 C7 C23 120.6(5) . 2_667 ?
C8 C7 C23 121.6(4) . 2_667 ?
C7 C8 C13 118.8(4) . . ?
C7 C8 C9 121.9(5) . . ?
C13 C8 C9 119.3(5) . . ?
C10 C9 C8 120.4(5) . . ?
C9 C10 C11 121.1(5) . . ?
C12 C11 C10 121.3(5) . . ?
C11 C12 C15 120.5(4) . . ?
C11 C12 C13 119.5(4) . . ?
C15 C12 C13 119.9(4) . . ?
C14 C13 C8 120.0(4) . . ?
C14 C13 C12 121.7(4) . . ?
C8 C13 C12 118.3(4) . . ?
C13 C14 C24 120.9(4) . 2_667 ?
C16 C15 C12 178.2(5) . . ?
C15 C16 C17 178.7(5) . . ?
C18 C17 C16 179.7(5) . . ?
C17 C18 C19 177.4(5) . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 C24 119.3(4) . . ?
C18 C19 C24 120.3(4) . . ?
C19 C20 C21 120.6(5) . . ?
C22 C21 C20 121.6(5) . . ?
C21 C22 C23 120.5(5) . . ?
C7 C23 C24 118.7(4) 2_667 . ?
C7 C23 C22 122.1(5) 2_667 . ?
C24 C23 C22 119.2(5) . . ?
C14 C24 C23 120.1(4) 2_667 . ?
C14 C24 C19 121.0(4) 2_667 . ?
C23 C24 C19 118.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.059