# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008


data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Yanhou Geng'
_publ_contact_author_email       YHGENG@CIAC.JL.CN

_publ_section_title              
;
Novel Spiro-Fluorenes from Tandem Radical-Addition for
Liquid Crystalline Monodisperse Conjugated Oligomers
;
loop_
_publ_author_name
'Yanhou Geng.'
'Laju Bu.'
'Yao Qu.'
'Lixiang Wang.'
'Fosong Wang.'
;
Xiaojie Zhang
;

# Attachment 'XJZhang3 R390.cif'

data_r390
_database_code_depnum_ccdc_archive 'CCDC 694714'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Br2 F9'
_chemical_formula_weight         624.19

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   33.150(3)
_cell_length_b                   13.5383(12)
_cell_length_c                   11.0627(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0360(10)
_cell_angle_gamma                90.00
_cell_volume                     4693.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2840
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.87

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    3.535
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_T_max  0.5799
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11987
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4141
_reflns_number_gt                2736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0642P)^2^+5.3724P] 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_extinction_coef       ?
_refine_ls_number_reflns         4141
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Br1 Br 0.220292(17) 1.11831(4) -0.03380(5) 0.0799(2) Uani 1 1 d . . .
Br2 Br 0.40913(2) 0.47415(4) 0.19408(7) 0.1058(3) Uani 1 1 d . . .
C1 C 0.24997(13) 0.9976(3) -0.0281(4) 0.0560(10) Uani 1 1 d . . .
C2 C 0.24384(13) 0.9453(3) -0.1403(4) 0.0581(11) Uani 1 1 d . . .
H2 H 0.2248 0.9682 -0.2170 0.070 Uiso 1 1 calc R . .
C3 C 0.26614(14) 0.8590(3) -0.1371(4) 0.0571(11) Uani 1 1 d . . .
H3 H 0.2626 0.8238 -0.2120 0.069 Uiso 1 1 calc R . .
C4 C 0.29395(12) 0.8247(3) -0.0217(4) 0.0482(9) Uani 1 1 d . . .
C5 C 0.29945(12) 0.8783(3) 0.0899(4) 0.0468(9) Uani 1 1 d . . .
C6 C 0.27758(13) 0.9650(3) 0.0884(4) 0.0524(10) Uani 1 1 d . . .
H6 H 0.2812 1.0006 0.1631 0.063 Uiso 1 1 calc R . .
C7 C 0.32036(13) 0.7361(3) 0.0095(4) 0.0521(10) Uani 1 1 d . . .
C8 C 0.32642(15) 0.6604(3) -0.0677(4) 0.0650(12) Uani 1 1 d . . .
H8 H 0.3126 0.6616 -0.1556 0.078 Uiso 1 1 calc R . .
C9 C 0.35329(16) 0.5833(4) -0.0116(5) 0.0731(13) Uani 1 1 d . . .
H9 H 0.3578 0.5321 -0.0619 0.088 Uiso 1 1 calc R . .
C10 C 0.37352(15) 0.5819(3) 0.1190(5) 0.0687(12) Uani 1 1 d . . .
C11 C 0.36845(13) 0.6577(3) 0.1970(4) 0.0578(11) Uani 1 1 d . . .
H11 H 0.3825 0.6563 0.2847 0.069 Uiso 1 1 calc R . .
C12 C 0.34186(12) 0.7355(3) 0.1406(4) 0.0495(10) Uani 1 1 d . . .
C13 C 0.33241(12) 0.8281(3) 0.2042(3) 0.0469(9) Uani 1 1 d . . .
C14 C 0.37245(13) 0.8942(3) 0.2593(4) 0.0516(10) Uani 1 1 d . . .
H14A H 0.3982 0.8544 0.2845 0.062 Uiso 1 1 calc R . .
H14B H 0.3743 0.9423 0.1964 0.062 Uiso 1 1 calc R . .
C15 C 0.36646(13) 0.9453(3) 0.3750(4) 0.0528(10) Uani 1 1 d . . .
H15 H 0.3443 0.9957 0.3430 0.063 Uiso 1 1 calc R . .
C16 C 0.34787(14) 0.8639(3) 0.4371(4) 0.0599(11) Uani 1 1 d . . .
H16 H 0.3319 0.8941 0.4882 0.072 Uiso 1 1 calc R . .
C17 C 0.31654(13) 0.8112(3) 0.3216(3) 0.0553(10) Uani 1 1 d . . .
H17A H 0.2881 0.8380 0.3038 0.066 Uiso 1 1 calc R . .
H17B H 0.3157 0.7411 0.3389 0.066 Uiso 1 1 calc R . .
C18 C 0.40605(14) 0.9969(3) 0.4639(4) 0.0575(11) Uani 1 1 d . . .
H18A H 0.4003 1.0174 0.5407 0.069 Uiso 1 1 calc R . .
H18B H 0.4294 0.9498 0.4891 0.069 Uiso 1 1 calc R . .
C19 C 0.41982(14) 1.0848(3) 0.4062(4) 0.0573(11) Uani 1 1 d . . .
C20 C 0.45321(15) 1.1501(3) 0.5000(4) 0.0632(12) Uani 1 1 d . . .
C21 C 0.47468(18) 1.2317(4) 0.4436(6) 0.0833(15) Uani 1 1 d . . .
C22 C 0.4984(2) 1.3111(5) 0.5323(7) 0.0994(18) Uani 1 1 d . . .
C23 C 0.38086(16) 0.7929(4) 0.5209(5) 0.0810(14) Uani 1 1 d . . .
H23A H 0.3960 0.7617 0.4707 0.121 Uiso 1 1 calc R . .
H23B H 0.3668 0.7435 0.5548 0.121 Uiso 1 1 calc R . .
H23C H 0.4006 0.8287 0.5900 0.121 Uiso 1 1 calc R . .
F1 F 0.43661(9) 1.0575(2) 0.3145(2) 0.0818(8) Uani 1 1 d . . .
F2 F 0.38628(9) 1.1433(2) 0.3449(3) 0.0971(10) Uani 1 1 d . . .
F3 F 0.48404(10) 1.0928(2) 0.5738(3) 0.1001(10) Uani 1 1 d . . .
F4 F 0.43447(11) 1.1936(3) 0.5766(3) 0.1140(12) Uani 1 1 d . . .
F5 F 0.50412(12) 1.1845(3) 0.4005(4) 0.1210(12) Uani 1 1 d . . .
F6 F 0.44694(13) 1.2721(3) 0.3417(4) 0.1364(16) Uani 1 1 d . . .
F7 F 0.52531(13) 1.2722(3) 0.6349(4) 0.1338(14) Uani 1 1 d . . .
F8 F 0.47255(15) 1.3676(3) 0.5669(6) 0.170(2) Uani 1 1 d . . .
F9 F 0.51970(15) 1.3668(3) 0.4777(5) 0.1549(17) 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
Br1 0.0857(4) 0.0743(4) 0.0788(4) 0.0134(3) 0.0254(3) 0.0238(3)
Br2 0.1093(5) 0.0670(4) 0.1331(6) 0.0007(3) 0.0284(4) 0.0276(3)
C1 0.051(2) 0.055(2) 0.061(3) 0.008(2) 0.018(2) -0.0012(19)
C2 0.056(3) 0.068(3) 0.045(2) 0.007(2) 0.009(2) -0.004(2)
C3 0.063(3) 0.066(3) 0.040(2) -0.005(2) 0.015(2) -0.014(2)
C4 0.049(2) 0.052(2) 0.043(2) -0.0027(18) 0.0142(19) -0.0129(19)
C5 0.044(2) 0.052(2) 0.045(2) 0.0009(19) 0.0151(18) -0.0048(18)
C6 0.055(2) 0.056(3) 0.047(2) -0.0017(19) 0.017(2) -0.002(2)
C7 0.056(2) 0.050(2) 0.052(3) -0.0057(19) 0.021(2) -0.0119(19)
C8 0.080(3) 0.058(3) 0.056(3) -0.015(2) 0.021(2) -0.011(2)
C9 0.087(4) 0.053(3) 0.086(4) -0.017(3) 0.037(3) -0.004(3)
C10 0.066(3) 0.056(3) 0.084(4) -0.001(3) 0.024(3) 0.003(2)
C11 0.058(3) 0.055(3) 0.060(3) 0.002(2) 0.018(2) -0.001(2)
C12 0.047(2) 0.054(2) 0.048(2) -0.0011(19) 0.0160(19) -0.0068(19)
C13 0.048(2) 0.052(2) 0.043(2) -0.0028(18) 0.0170(18) -0.0019(18)
C14 0.052(2) 0.063(3) 0.041(2) -0.0027(19) 0.0181(19) -0.0055(19)
C15 0.053(2) 0.060(3) 0.047(2) -0.0034(19) 0.0171(19) -0.005(2)
C16 0.064(3) 0.075(3) 0.045(2) -0.003(2) 0.024(2) -0.009(2)
C17 0.056(2) 0.063(3) 0.047(2) 0.002(2) 0.017(2) -0.004(2)
C18 0.070(3) 0.060(3) 0.045(2) -0.004(2) 0.021(2) -0.004(2)
C19 0.055(3) 0.056(3) 0.059(3) -0.003(2) 0.017(2) 0.004(2)
C20 0.065(3) 0.061(3) 0.065(3) -0.010(2) 0.022(3) -0.002(2)
C21 0.069(3) 0.074(3) 0.100(4) -0.001(3) 0.018(3) -0.013(3)
C22 0.082(4) 0.082(4) 0.132(6) -0.002(4) 0.032(4) -0.013(4)
C23 0.079(3) 0.086(4) 0.067(3) 0.016(3) 0.010(3) -0.016(3)
F1 0.100(2) 0.091(2) 0.0633(16) -0.0169(14) 0.0388(16) -0.0277(16)
F2 0.0670(18) 0.0756(19) 0.129(3) 0.0183(18) 0.0043(17) -0.0001(15)
F3 0.083(2) 0.093(2) 0.092(2) 0.0126(17) -0.0147(17) -0.0124(17)
F4 0.124(3) 0.119(3) 0.124(3) -0.064(2) 0.074(2) -0.043(2)
F5 0.121(3) 0.133(3) 0.134(3) -0.028(2) 0.075(2) -0.032(2)
F6 0.131(3) 0.099(3) 0.129(3) 0.048(2) -0.026(2) -0.036(2)
F7 0.105(3) 0.135(3) 0.129(3) -0.012(3) -0.006(2) -0.030(2)
F8 0.140(4) 0.103(3) 0.278(6) -0.073(4) 0.082(4) -0.018(3)
F9 0.164(4) 0.121(3) 0.181(4) -0.004(3) 0.059(3) -0.071(3)

_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
Br1 C1 1.898(4) . ?
Br2 C10 1.890(5) . ?
C1 C2 1.385(6) . ?
C1 C6 1.387(6) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 C7 1.459(6) . ?
C5 C6 1.378(5) . ?
C5 C13 1.534(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(6) . ?
C7 C12 1.392(5) . ?
C8 C9 1.381(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(6) . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.519(5) . ?
C13 C14 1.551(5) . ?
C13 C17 1.568(5) . ?
C14 C15 1.524(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.530(6) . ?
C15 C18 1.528(6) . ?
C15 H15 0.9800 . ?
C16 C23 1.522(7) . ?
C16 C17 1.535(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.491(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 F2 1.354(5) . ?
C19 F1 1.358(5) . ?
C19 C20 1.528(6) . ?
C20 F3 1.330(5) . ?
C20 F4 1.340(5) . ?
C20 C21 1.551(7) . ?
C21 F6 1.319(6) . ?
C21 F5 1.375(6) . ?
C21 C22 1.495(8) . ?
C22 F8 1.297(7) . ?
C22 F7 1.304(7) . ?
C22 F9 1.307(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 C6 122.0(4) . . ?
C2 C1 Br1 119.2(3) . . ?
C6 C1 Br1 118.8(3) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 C7 131.3(4) . . ?
C5 C4 C7 108.9(3) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 C13 128.2(4) . . ?
C4 C5 C13 110.6(3) . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
C8 C7 C12 120.6(4) . . ?
C8 C7 C4 131.0(4) . . ?
C12 C7 C4 108.4(3) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 Br2 119.4(4) . . ?
C11 C10 Br2 118.9(4) . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C7 120.5(4) . . ?
C11 C12 C13 128.0(4) . . ?
C7 C12 C13 111.4(3) . . ?
C12 C13 C5 100.5(3) . . ?
C12 C13 C14 112.2(3) . . ?
C5 C13 C14 110.9(3) . . ?
C12 C13 C17 116.0(3) . . ?
C5 C13 C17 113.9(3) . . ?
C14 C13 C17 103.5(3) . . ?
C15 C14 C13 105.2(3) . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C14 C15 C16 103.4(3) . . ?
C14 C15 C18 115.4(3) . . ?
C16 C15 C18 115.3(3) . . ?
C14 C15 H15 107.4 . . ?
C16 C15 H15 107.4 . . ?
C18 C15 H15 107.4 . . ?
C23 C16 C15 114.4(4) . . ?
C23 C16 C17 111.8(4) . . ?
C15 C16 C17 102.9(3) . . ?
C23 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
C16 C17 C13 107.6(3) . . ?
C16 C17 H17A 110.2 . . ?
C13 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
C13 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C19 C18 C15 114.1(3) . . ?
C19 C18 H18A 108.7 . . ?
C15 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C15 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
F2 C19 F1 104.8(4) . . ?
F2 C19 C18 111.4(4) . . ?
F1 C19 C18 111.1(4) . . ?
F2 C19 C20 107.2(4) . . ?
F1 C19 C20 106.4(3) . . ?
C18 C19 C20 115.3(4) . . ?
F3 C20 F4 106.9(4) . . ?
F3 C20 C19 108.7(4) . . ?
F4 C20 C19 107.5(4) . . ?
F3 C20 C21 107.5(4) . . ?
F4 C20 C21 108.0(4) . . ?
C19 C20 C21 117.7(4) . . ?
F6 C21 F5 105.8(5) . . ?
F6 C21 C22 109.5(5) . . ?
F5 C21 C22 106.3(5) . . ?
F6 C21 C20 110.8(4) . . ?
F5 C21 C20 106.2(4) . . ?
C22 C21 C20 117.4(5) . . ?
F8 C22 F7 108.2(7) . . ?
F8 C22 F9 107.7(6) . . ?
F7 C22 F9 108.4(6) . . ?
F8 C22 C21 111.2(6) . . ?
F7 C22 C21 110.2(6) . . ?
F9 C22 C21 111.1(6) . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.061