# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_snu3
#TrackingRef 'CCDC 773768.cif'


_audit_creation_date             2013-04-22T14:04:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C44 H26'
_chemical_formula_sum            'C44 H26'
_chemical_formula_weight         554.65

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_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                   8.0943(4)
_cell_length_b                   8.7229(4)
_cell_length_c                   10.6687(5)
_cell_angle_alpha                99.129(3)
_cell_angle_beta                 90.439(3)
_cell_angle_gamma                114.943(2)
_cell_volume                     672.02(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.1947
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_number            8866
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_full        27.6
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             3107
_reflns_number_gt                2419
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.1210P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3107
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2041
_refine_ls_wR_factor_gt          0.1927
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.103

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.04879(17) -0.40498(14) 0.52199(11) 0.0190(3) Uani 1 1 d . . .
C2 C 0.02798(19) -0.32774(16) 0.64229(12) 0.0240(3) Uani 1 1 d . . .
H2 H -0.0488 -0.3957 0.6957 0.029 Uiso 1 1 calc R . .
C3 C 0.1199(2) -0.15138(16) 0.68351(12) 0.0252(4) Uani 1 1 d . . .
H3 H 0.1047 -0.1038 0.7645 0.03 Uiso 1 1 calc R . .
C4 C 0.23408(19) -0.04440(16) 0.60630(12) 0.0214(3) Uani 1 1 d . . .
C5 C 0.2528(2) -0.12050(16) 0.48523(12) 0.0264(4) Uani 1 1 d . . .
H5 H 0.3262 -0.0518 0.4308 0.032 Uiso 1 1 calc R . .
C6 C 0.1637(2) -0.29712(16) 0.44487(12) 0.0259(4) Uani 1 1 d . . .
H6 H 0.1811 -0.3447 0.3645 0.031 Uiso 1 1 calc R . .
C7 C 0.32498(19) 0.14648(16) 0.64517(12) 0.0206(3) Uani 1 1 d . . .
C8 C 0.45323(18) 0.22894(16) 0.75253(12) 0.0189(3) Uani 1 1 d . . .
C9 C 0.53223(18) 0.41210(16) 0.78387(12) 0.0193(3) Uani 1 1 d . . .
C10 C 0.48442(19) 0.50866(16) 0.70791(12) 0.0211(3) Uani 1 1 d . . .
C11 C 0.3577(2) 0.42211(17) 0.60223(12) 0.0236(3) Uani 1 1 d . . .
H11 H 0.3253 0.4843 0.5516 0.028 Uiso 1 1 calc R . .
C12 C 0.27997(19) 0.24433(17) 0.57233(12) 0.0234(3) Uani 1 1 d . . .
H12 H 0.1956 0.189 0.5018 0.028 Uiso 1 1 calc R . .
C13 C 0.51004(19) 0.13776(16) 0.83116(12) 0.0228(3) Uani 1 1 d . . .
H13 H 0.4639 0.0188 0.8099 0.027 Uiso 1 1 calc R . .
C14 C 0.6295(2) 0.22105(17) 0.93588(12) 0.0246(3) Uani 1 1 d . . .
H14 H 0.6621 0.1578 0.9853 0.03 Uiso 1 1 calc R . .
C15 C 0.70677(19) 0.40519(17) 0.97189(12) 0.0228(3) Uani 1 1 d . . .
C16 C 0.65959(19) 0.49906(16) 0.89370(12) 0.0204(3) Uani 1 1 d . . .
C17 C 0.7368(2) 0.68210(17) 0.92521(13) 0.0234(4) Uani 1 1 d . . .
C18 C 0.6860(2) 0.77529(16) 0.84549(14) 0.0271(4) Uani 1 1 d . . .
H18 H 0.7365 0.8946 0.8655 0.032 Uiso 1 1 calc R . .
C19 C 0.5660(2) 0.69334(17) 0.74175(13) 0.0257(4) Uani 1 1 d . . .
H19 H 0.5357 0.7571 0.6915 0.031 Uiso 1 1 calc R . .
C20 C 0.8267(2) 0.49248(19) 1.08155(13) 0.0286(4) Uani 1 1 d . . .
H20 H 0.8571 0.4309 1.1339 0.034 Uiso 1 1 calc R . .
C21 C 0.9002(2) 0.6703(2) 1.11224(13) 0.0310(4) Uani 1 1 d . . .
H21 H 0.9796 0.7271 1.1851 0.037 Uiso 1 1 calc R . .
C22 C 0.8569(2) 0.76344(18) 1.03591(13) 0.0284(4) Uani 1 1 d . . .
H22 H 0.908 0.8826 1.0579 0.034 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
C1 0.0228(7) 0.0206(7) 0.0150(6) -0.0011(5) -0.0023(5) 0.0122(5)
C2 0.0308(8) 0.0227(7) 0.0168(6) 0.0021(5) 0.0020(5) 0.0104(5)
C3 0.0329(8) 0.0248(7) 0.0153(6) -0.0024(5) 0.0031(5) 0.0119(6)
C4 0.0246(7) 0.0212(6) 0.0182(6) -0.0012(5) -0.0022(5) 0.0114(5)
C5 0.0321(8) 0.0236(7) 0.0207(7) 0.0018(5) 0.0059(6) 0.0099(6)
C6 0.0334(8) 0.0236(7) 0.0179(7) -0.0025(5) 0.0052(5) 0.0114(6)
C7 0.0249(7) 0.0207(6) 0.0167(6) 0.0001(5) 0.0024(5) 0.0114(5)
C8 0.0228(7) 0.0213(6) 0.0142(6) 0.0005(5) 0.0025(5) 0.0117(5)
C9 0.0222(7) 0.0202(6) 0.0160(7) 0.0004(5) 0.0027(5) 0.0106(5)
C10 0.0261(7) 0.0212(6) 0.0180(7) 0.0022(5) 0.0048(5) 0.0125(5)
C11 0.0293(8) 0.0270(7) 0.0195(7) 0.0061(5) 0.0022(5) 0.0161(6)
C12 0.0260(7) 0.0266(7) 0.0169(6) 0.0007(5) -0.0027(5) 0.0116(6)
C13 0.0282(7) 0.0214(6) 0.0206(7) 0.0018(5) 0.0017(5) 0.0131(5)
C14 0.0301(8) 0.0304(7) 0.0190(7) 0.0049(5) 0.0010(5) 0.0182(6)
C15 0.0227(7) 0.0298(7) 0.0167(7) -0.0002(5) 0.0027(5) 0.0134(6)
C16 0.0214(7) 0.0244(7) 0.0148(7) -0.0013(5) 0.0035(5) 0.0110(5)
C17 0.0243(7) 0.0241(7) 0.0183(7) -0.0022(5) 0.0051(5) 0.0090(5)
C18 0.0319(8) 0.0194(6) 0.0279(7) 0.0006(5) 0.0076(6) 0.0103(6)
C19 0.0334(8) 0.0216(7) 0.0259(7) 0.0053(5) 0.0070(6) 0.0149(6)
C20 0.0286(8) 0.0407(8) 0.0183(7) 0.0005(6) 0.0000(6) 0.0181(6)
C21 0.0256(8) 0.0412(8) 0.0182(7) -0.0068(6) -0.0009(5) 0.0109(6)
C22 0.0274(8) 0.0275(7) 0.0215(7) -0.0066(5) 0.0042(6) 0.0071(6)


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.3952(18) . ?
C1 C2 1.3979(17) . ?
C1 C1 1.495(2) 2_546 ?
C2 C3 1.3887(17) . ?
C3 C4 1.3899(19) . ?
C4 C5 1.3957(18) . ?
C4 C7 1.4928(16) . ?
C5 C6 1.3880(17) . ?
C7 C12 1.3905(19) . ?
C7 C8 1.4133(18) . ?
C8 C9 1.4279(17) . ?
C8 C13 1.4360(19) . ?
C9 C10 1.415(2) . ?
C9 C16 1.4321(19) . ?
C10 C11 1.3973(19) . ?
C10 C19 1.4409(17) . ?
C11 C12 1.3855(17) . ?
C13 C14 1.3583(19) . ?
C14 C15 1.4395(18) . ?
C15 C20 1.4026(19) . ?
C15 C16 1.410(2) . ?
C16 C17 1.4274(17) . ?
C17 C22 1.406(2) . ?
C17 C18 1.432(2) . ?
C18 C19 1.351(2) . ?
C20 C21 1.3875(19) . ?
C21 C22 1.375(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
C6 C1 C2 117.15(11) . . ?
C6 C1 C1 121.59(13) . 2_546 ?
C2 C1 C1 121.25(14) . 2_546 ?
C3 C2 C1 121.23(12) . . ?
C2 C3 C4 121.42(11) . . ?
C3 C4 C5 117.59(12) . . ?
C3 C4 C7 122.39(11) . . ?
C5 C4 C7 119.89(12) . . ?
C6 C5 C4 121.02(12) . . ?
C5 C6 C1 121.57(11) . . ?
C12 C7 C8 119.73(12) . . ?
C12 C7 C4 118.06(11) . . ?
C8 C7 C4 122.21(12) . . ?
C7 C8 C9 118.60(12) . . ?
C7 C8 C13 123.25(12) . . ?
C9 C8 C13 118.15(12) . . ?
C10 C9 C8 120.53(12) . . ?
C10 C9 C16 119.60(12) . . ?
C8 C9 C16 119.86(13) . . ?
C11 C10 C9 119.04(12) . . ?
C11 C10 C19 121.56(13) . . ?
C9 C10 C19 119.40(12) . . ?
C12 C11 C10 120.45(13) . . ?
C11 C12 C7 121.66(12) . . ?
C14 C13 C8 121.60(12) . . ?
C13 C14 C15 121.34(13) . . ?
C20 C15 C16 119.62(13) . . ?
C20 C15 C14 121.93(13) . . ?
C16 C15 C14 118.44(12) . . ?
C15 C16 C17 119.85(13) . . ?
C15 C16 C9 120.53(12) . . ?
C17 C16 C9 119.61(13) . . ?
C22 C17 C16 118.28(14) . . ?
C22 C17 C18 122.58(13) . . ?
C16 C17 C18 119.12(12) . . ?
C19 C18 C17 121.31(12) . . ?
C18 C19 C10 120.96(14) . . ?
C21 C20 C15 120.25(14) . . ?
C22 C21 C20 120.66(13) . . ?
C21 C22 C17 121.32(13) . . ?



_chemical_name_common            "4,4'-dipyrenyl-biphenyl ?"
_database_code_depnum_ccdc_archive 'CCDC 773768'