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


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Jun Wei'
_publ_contact_author_email       wjjin@bnu.edu.cn
_publ_contact_author_name        'Jun Wei'

data_110510b_0m
_database_code_depnum_ccdc_archive 'CCDC 856554'
#TrackingRef '- 110510b_0m.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C24 H8 F8 I4 N'

_chemical_formula_weight         969.91

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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                   5.9625(11)

_cell_length_b                   9.3712(18)

_cell_length_c                   12.051(2)

_cell_angle_alpha                75.207(3)

_cell_angle_beta                 88.706(3)

_cell_angle_gamma                80.057(3)

_cell_volume                     641.1(2)

_cell_formula_units_Z            1

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    1343

_cell_measurement_theta_min      2.28

_cell_measurement_theta_max      27.43

_exptl_crystal_description       ?

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.20

_exptl_crystal_size_mid          0.12

_exptl_crystal_size_min          0.05

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.512

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             443

_exptl_absorpt_coefficient_mu    4.934

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.4386

_exptl_absorpt_correction_T_max  0.7905

_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      150(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            3264

_diffrn_reflns_av_R_equivalents  0.0200

_diffrn_reflns_av_sigmaI/netI    0.0399

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       14

_diffrn_reflns_theta_min         2.28

_diffrn_reflns_theta_max         25.25

_reflns_number_total             2296

_reflns_number_gt                1912

_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^)+(0.0413P)^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_extinction_coef       ?

_refine_ls_number_reflns         2296

_refine_ls_number_parameters     196

_refine_ls_number_restraints     6

_refine_ls_R_factor_all          0.0410

_refine_ls_R_factor_gt           0.0325

_refine_ls_wR_factor_ref         0.0789

_refine_ls_wR_factor_gt          0.0746

_refine_ls_goodness_of_fit_ref   1.018

_refine_ls_restrained_S_all      1.018

_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

C1 C 0.8878(9) 0.7210(6) 0.4758(4) 0.0232(12) Uani 1 1 d . A 1
C2 C 1.0618(9) 0.8036(6) 0.4501(4) 0.0230(12) Uani 1 1 d . A 1
C3 C 1.1798(9) 0.8335(6) 0.5370(5) 0.0263(13) Uani 1 1 d . A 1
C4 C 1.1287(9) 0.7837(6) 0.6513(4) 0.0224(12) Uani 1 1 d . A 1
C5 C 0.9560(9) 0.7010(7) 0.6751(5) 0.0275(13) Uani 1 1 d . A 1
C6 C 0.8364(9) 0.6691(6) 0.5906(5) 0.0240(12) Uani 1 1 d . A 1
C7 C 0.3606(9) 0.8927(6) 1.0642(6) 0.035(5) Uani 0.50 1 d PG B -1
C8 C 0.3025(12) 0.7537(7) 1.1153(7) 0.035(4) Uani 0.50 1 d PG B -1
H8 H 0.1610 0.7479 1.1526 0.043 Uiso 0.50 1 calc PR B -1
C9 C 0.4512(14) 0.6234(6) 1.1118(6) 0.033(4) Uani 0.50 1 d PG B -1
H9 H 0.4115 0.5284 1.1468 0.040 Uiso 0.50 1 calc PR B -1
C10 C 0.6582(13) 0.6319(5) 1.0572(5) 0.025(4) Uani 0.50 1 d PG B -1
H10 H 0.7598 0.5428 1.0549 0.030 Uiso 0.50 1 calc PR B -1
C11 C 0.7163(10) 0.7709(5) 1.0061(5) 0.024(4) Uani 0.50 1 d PG B -1
H11 H 0.8577 0.7767 0.9688 0.029 Uiso 0.50 1 calc PR B -1
C12 C 0.5675(8) 0.9013(5) 1.0096(4) 0.023(4) Uani 0.50 1 d PG B -1
C13 C 0.5554(9) 1.0654(5) 0.9693(4) 0.024(3) Uani 0.50 1 d PG B -1
C14 C 0.7118(10) 1.1470(6) 0.9076(5) 0.023(3) Uani 0.50 1 d PG B -1
H14 H 0.8510 1.0964 0.8856 0.027 Uiso 0.50 1 calc PR B -1
C15 C 0.6646(14) 1.3027(6) 0.8781(5) 0.026(4) Uani 0.50 1 d PGU B -1
H15 H 0.7715 1.3585 0.8359 0.032 Uiso 0.50 1 calc PR B -1
C16 C 0.4609(15) 1.3768(5) 0.9103(6) 0.049(6) Uani 0.50 1 d PG B -1
H16 H 0.4286 1.4832 0.8901 0.058 Uiso 0.50 1 calc PR B -1
C17 C 0.3045(13) 1.2951(6) 0.9720(7) 0.040(6) Uani 0.50 1 d PG B -1
H17 H 0.1653 1.3458 0.9940 0.048 Uiso 0.50 1 calc PR B -1
C18 C 0.3518(10) 1.1394(6) 1.0015(6) 0.030(5) Uani 0.50 1 d PG B -1
F1 F 1.1195(5) 0.8576(4) 0.3419(3) 0.0350(8) Uani 1 1 d . . .
F2 F 1.3461(5) 0.9164(4) 0.5075(3) 0.0381(9) Uani 1 1 d . . .
F3 F 0.9025(6) 0.6433(4) 0.7858(3) 0.0407(9) Uani 1 1 d . . .
F4 F 0.6722(6) 0.5865(4) 0.6196(3) 0.0409(9) Uani 1 1 d . . .
I1 I 0.70851(6) 0.67927(4) 0.34481(3) 0.03206(14) Uani 1 1 d . . .
I2 I 1.30852(6) 0.82892(4) 0.78062(3) 0.03288(14) Uani 1 1 d . . .
N1 N 0.2266(17) 1.0301(13) 1.0599(8) 0.036(2) Uani 0.50 1 d P B -1

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 0.023(3) 0.025(3) 0.023(3) -0.008(2) -0.006(2) -0.002(2)
C2 0.028(3) 0.023(3) 0.016(3) -0.001(2) -0.002(2) -0.004(2)
C3 0.019(3) 0.022(3) 0.036(3) -0.004(3) -0.002(2) -0.004(2)
C4 0.023(3) 0.023(3) 0.021(3) -0.008(2) -0.005(2) 0.000(2)
C5 0.023(3) 0.036(3) 0.023(3) -0.005(3) -0.002(2) -0.004(3)
C6 0.028(3) 0.022(3) 0.025(3) -0.008(2) -0.005(2) -0.007(2)
C7 0.025(9) 0.059(12) 0.023(9) -0.006(8) 0.001(7) -0.017(8)
C8 0.065(10) 0.027(10) 0.018(8) -0.009(6) 0.000(7) -0.015(8)
C9 0.032(9) 0.037(10) 0.031(8) -0.010(7) -0.002(7) -0.008(7)
C10 0.040(9) 0.015(9) 0.020(8) -0.002(6) -0.004(6) -0.007(7)
C11 0.037(9) 0.019(12) 0.015(6) -0.003(8) -0.001(5) -0.007(7)
C12 0.017(9) 0.033(9) 0.022(7) -0.013(7) 0.005(6) -0.005(8)
C13 0.032(10) 0.033(9) 0.014(8) -0.012(6) -0.005(7) -0.014(7)
C14 0.035(8) 0.026(7) 0.011(6) -0.013(6) -0.004(6) -0.005(7)
C15 0.043(7) 0.018(7) 0.018(6) 0.005(5) -0.011(6) -0.017(6)
C16 0.067(16) 0.048(12) 0.028(10) -0.004(8) -0.029(11) -0.009(9)
C17 0.065(12) 0.022(15) 0.030(10) -0.015(9) -0.029(8) 0.013(8)
C18 0.040(11) 0.034(10) 0.017(7) -0.010(8) -0.016(7) -0.002(10)
F1 0.0297(17) 0.052(2) 0.0223(17) -0.0041(16) 0.0050(14) -0.0120(16)
F2 0.0305(18) 0.050(2) 0.038(2) -0.0072(17) 0.0013(15) -0.0252(17)
F3 0.044(2) 0.056(2) 0.0213(18) -0.0001(16) -0.0020(15) -0.0206(18)
F4 0.043(2) 0.051(2) 0.033(2) -0.0058(17) -0.0004(16) -0.0291(19)
I1 0.0336(2) 0.0346(3) 0.0312(2) -0.01361(18) -0.01120(17) -0.00537(18)
I2 0.0337(2) 0.0387(3) 0.0293(2) -0.01311(18) -0.01051(17) -0.00654(19)
N1 0.038(6) 0.052(7) 0.021(5) -0.015(5) 0.000(4) -0.007(5)

_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 1.382(7) . ?
C1 C6 1.391(7) . ?
C1 I1 2.079(5) . ?
C2 F1 1.334(6) . ?
C2 C3 1.386(8) . ?
C3 F2 1.350(6) . ?
C3 C4 1.382(8) . ?
C4 C5 1.376(7) . ?
C4 I2 2.080(5) . ?
C5 F3 1.358(6) . ?
C5 C6 1.377(7) . ?
C6 F4 1.337(6) . ?
C7 N1 1.383(12) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.4792 . ?
C13 C18 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3901 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 N1 1.405(12) . ?

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 118.0(5) . . ?
C2 C1 I1 120.3(4) . . ?
C6 C1 I1 121.7(4) . . ?
F1 C2 C1 121.3(5) . . ?
F1 C2 C3 118.2(5) . . ?
C1 C2 C3 120.5(5) . . ?
F2 C3 C4 119.8(5) . . ?
F2 C3 C2 118.2(5) . . ?
C4 C3 C2 122.0(5) . . ?
C5 C4 C3 116.7(5) . . ?
C5 C4 I2 121.9(4) . . ?
C3 C4 I2 121.4(4) . . ?
F3 C5 C4 119.9(5) . . ?
F3 C5 C6 117.4(5) . . ?
C4 C5 C6 122.6(5) . . ?
F4 C6 C5 119.6(5) . . ?
F4 C6 C1 120.1(5) . . ?
C5 C6 C1 120.2(5) . . ?
N1 C7 C8 125.7(5) . . ?
N1 C7 C12 114.3(5) . . ?
C8 C7 C12 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 C13 138.8 . . ?
C7 C12 C13 101.2 . . ?
C18 C13 C14 120.0 . . ?
C18 C13 C12 110.3 . . ?
C14 C13 C12 129.7 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 N1 132.4(5) . . ?
C13 C18 N1 107.6(5) . . ?
C7 N1 C18 106.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        25.25

_diffrn_measured_fraction_theta_full 0.985

_refine_diff_density_max         0.785

_refine_diff_density_min         -0.725

_refine_diff_density_rms         0.136