# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_kes48
_database_code_depnum_ccdc_archive 'CCDC 1478328'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,4-bis(5-phenylfuran-2-yl)benzene 
;
_chemical_name_common            'furan/phenylene co-oligomer BPFB'
_chemical_melting_point          514
_chemical_formula_moiety         'C26 H18 O2'
_chemical_formula_sum            'C26 H18 O2'
_chemical_formula_weight         362.40

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   'P2(1)/c  '

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

_cell_length_a                   20.4117(19)
_cell_length_b                   7.2937(8)
_cell_length_c                   6.2000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.731(3)
_cell_angle_gamma                90.00
_cell_volume                     914.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4338
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.72

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7800
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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_reflns_number            15386
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.01
_diffrn_reflns_theta_max         25.09
_reflns_number_total             1628
_reflns_number_gt                1264
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0719P)²+0.0251P] 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_number_reflns         1628
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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
O1 O 0.81903(5) 1.00976(15) 0.01362(16) 0.0272(3) Uani 1 1 d . . .
C1 C 0.57389(8) 1.0162(3) -0.2380(3) 0.0377(5) Uani 1 1 d . . .
H1 H 0.5308 1.0254 -0.3169 0.045 Uiso 1 1 calc R . .
C2 C 0.62734(8) 1.0899(2) -0.3222(3) 0.0354(4) Uani 1 1 d . . .
H4 H 0.6210 1.1488 -0.4601 0.043 Uiso 1 1 calc R . .
C3 C 0.69010(8) 1.0784(2) -0.2067(2) 0.0304(4) Uani 1 1 d . . .
H3 H 0.7266 1.1299 -0.2655 0.036 Uiso 1 1 calc R . .
C4 C 0.70015(8) 0.9917(2) -0.0046(2) 0.0261(4) Uani 1 1 d . . .
C5 C 0.76541(8) 0.9758(2) 0.1208(3) 0.0267(4) Uani 1 1 d . . .
C6 C 0.87497(7) 0.9742(2) 0.1580(2) 0.0259(4) Uani 1 1 d . . .
C7 C 0.93818(7) 0.9891(2) 0.0765(2) 0.0252(4) Uani 1 1 d . . .
C8 C 0.99521(7) 0.9173(2) 0.1977(2) 0.0273(4) Uani 1 1 d . . .
H6 H 0.9922 0.8603 0.3338 0.033 Uiso 1 1 calc R . .
C9 C 0.94440(8) 1.0719(2) -0.1227(2) 0.0276(4) Uani 1 1 d . . .
H9 H 0.9064 1.1216 -0.2079 0.033 Uiso 1 1 calc R . .
C10 C 0.58335(8) 0.9286(2) -0.0377(3) 0.0359(4) Uani 1 1 d . . .
H2 H 0.5467 0.8768 0.0199 0.043 Uiso 1 1 calc R . .
C11 C 0.64558(8) 0.9165(2) 0.0779(3) 0.0321(4) Uani 1 1 d . . .
H7 H 0.6516 0.8564 0.2150 0.038 Uiso 1 1 calc R . .
C12 C 0.78714(8) 0.9240(2) 0.3279(3) 0.0313(4) Uani 1 1 d . . .
H8 H 0.7604 0.8938 0.4369 0.038 Uiso 1 1 calc R . .
C13 C 0.85697(8) 0.9233(2) 0.3518(3) 0.0316(4) Uani 1 1 d . . .
H5 H 0.8859 0.8927 0.4798 0.038 Uiso 1 1 calc R . .

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 0.0261(6) 0.0278(6) 0.0276(6) 0.0038(4) 0.0035(5) 0.0005(4)
C1 0.0311(10) 0.0390(11) 0.0415(11) -0.0048(8) -0.0005(8) 0.0052(8)
C2 0.0399(10) 0.0345(10) 0.0314(9) 0.0025(7) 0.0030(7) 0.0041(8)
C3 0.0335(9) 0.0271(9) 0.0319(9) 0.0011(7) 0.0096(7) 0.0004(7)
C4 0.0287(9) 0.0209(8) 0.0294(9) -0.0026(6) 0.0070(7) 0.0041(6)
C5 0.0291(8) 0.0214(8) 0.0311(9) 0.0001(7) 0.0090(7) 0.0002(6)
C6 0.0275(9) 0.0209(8) 0.0277(8) -0.0005(6) -0.0021(7) 0.0010(6)
C7 0.0278(9) 0.0193(8) 0.0275(9) -0.0025(6) -0.0006(7) -0.0022(6)
C8 0.0318(9) 0.0231(8) 0.0262(8) 0.0020(6) 0.0016(7) -0.0014(7)
C9 0.0283(9) 0.0251(9) 0.0274(8) -0.0001(7) -0.0035(7) 0.0007(7)
C10 0.0292(9) 0.0363(10) 0.0439(10) 0.0008(8) 0.0118(8) 0.0008(7)
C11 0.0334(9) 0.0302(9) 0.0340(9) 0.0034(7) 0.0095(7) 0.0032(7)
C12 0.0358(10) 0.0302(10) 0.0295(9) 0.0018(7) 0.0100(7) 0.0008(7)
C13 0.0363(9) 0.0302(10) 0.0274(8) 0.0014(7) 0.0007(7) 0.0013(7)

_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 C5 1.3770(18) . ?
O1 C6 1.3774(18) . ?
C1 C2 1.380(2) . ?
C1 C10 1.387(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H4 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.399(2) . ?
C4 C5 1.454(2) . ?
C5 C12 1.355(2) . ?
C6 C13 1.355(2) . ?
C6 C7 1.452(2) . ?
C7 C9 1.396(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.377(2) 3_775 ?
C8 H6 0.9500 . ?
C9 C8 1.377(2) 3_775 ?
C9 H9 0.9500 . ?
C10 C11 1.375(2) . ?
C10 H2 0.9500 . ?
C11 H7 0.9500 . ?
C12 C13 1.413(2) . ?
C12 H8 0.9500 . ?
C13 H5 0.9500 . ?

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
C5 O1 C6 107.21(11) . . ?
C2 C1 C10 119.76(15) . . ?
C2 C1 H1 120.1 . . ?
C10 C1 H1 120.1 . . ?
C1 C2 C3 120.30(15) . . ?
C1 C2 H4 119.9 . . ?
C3 C2 H4 119.9 . . ?
C2 C3 C4 120.45(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C11 118.58(14) . . ?
C3 C4 C5 122.01(14) . . ?
C11 C4 C5 119.40(14) . . ?
C12 C5 O1 109.11(13) . . ?
C12 C5 C4 133.51(14) . . ?
O1 C5 C4 117.29(13) . . ?
C13 C6 O1 109.14(13) . . ?
C13 C6 C7 133.56(14) . . ?
O1 C6 C7 117.22(12) . . ?
C9 C7 C8 117.96(14) . . ?
C9 C7 C6 122.10(14) . . ?
C8 C7 C6 119.94(14) . . ?
C9 C8 C7 121.02(14) 3_775 . ?
C9 C8 H6 119.5 3_775 . ?
C7 C8 H6 119.5 . . ?
C8 C9 C7 121.03(14) 3_775 . ?
C8 C9 H9 119.5 3_775 . ?
C7 C9 H9 119.5 . . ?
C11 C10 C1 120.26(15) . . ?
C11 C10 H2 119.9 . . ?
C1 C10 H2 119.9 . . ?
C10 C11 C4 120.65(15) . . ?
C10 C11 H7 119.7 . . ?
C4 C11 H7 119.7 . . ?
C5 C12 C13 107.29(14) . . ?
C5 C12 H8 126.4 . . ?
C13 C12 H8 126.4 . . ?
C6 C13 C12 107.24(15) . . ?
C6 C13 H5 126.4 . . ?
C12 C13 H5 126.4 . . ?

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
C10 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C11 0.2(2) . . . . ?
C2 C3 C4 C5 179.54(14) . . . . ?
C6 O1 C5 C12 1.21(17) . . . . ?
C6 O1 C5 C4 -175.84(13) . . . . ?
C3 C4 C5 C12 168.91(17) . . . . ?
C11 C4 C5 C12 -11.8(3) . . . . ?
C3 C4 C5 O1 -14.9(2) . . . . ?
C11 C4 C5 O1 164.36(13) . . . . ?
C5 O1 C6 C13 -1.29(17) . . . . ?
C5 O1 C6 C7 176.05(12) . . . . ?
C13 C6 C7 C9 -170.25(17) . . . . ?
O1 C6 C7 C9 13.2(2) . . . . ?
C13 C6 C7 C8 10.4(3) . . . . ?
O1 C6 C7 C8 -166.09(13) . . . . ?
C9 C7 C8 C9 0.0(2) . . . 3_775 ?
C6 C7 C8 C9 179.34(13) . . . 3_775 ?
C8 C7 C9 C8 0.0(2) . . . 3_775 ?
C6 C7 C9 C8 -179.32(13) . . . 3_775 ?
C2 C1 C10 C11 0.6(3) . . . . ?
C1 C10 C11 C4 -0.1(2) . . . . ?
C3 C4 C11 C10 -0.3(2) . . . . ?
C5 C4 C11 C10 -179.63(14) . . . . ?
O1 C5 C12 C13 -0.68(18) . . . . ?
C4 C5 C12 C13 175.71(17) . . . . ?
O1 C6 C13 C12 0.88(18) . . . . ?
C7 C6 C13 C12 -175.86(16) . . . . ?
C5 C12 C13 C6 -0.13(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_exptl_crystal_recrystallization_method 'solvent-antisolvent crystallization'
_exptl_crystal_preparation       Luminescent
