# 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

_publ_contact_author_name        'Xiao Yi'
_publ_contact_author_email       XIAOYI@CHEM.DLUT.EDU.CN

_publ_section_title              
;
Bulky 4-tritylphenylethynyl substituted
boradiazaindacene: Pure red emission, relatively large Stokes shift and
inhibition of self-quenching
;
loop_
_publ_author_name
'Xiao Yi.'
'Yunqi Liu.'
'Xuhong Qian.'
'Yugeng Wen.'
'Gui Yu.'
'Dakui Zhang.'

# Attachment 'CIF for compound 4.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 650117'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H27 B F2 N2'
_chemical_formula_sum            'C35 H27 B F2 N2'
_chemical_formula_weight         524.40

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 0.0000 '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'
B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Fdd2 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   28.6219(16)
_cell_length_b                   6.9589(4)
_cell_length_c                   28.2896(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5634.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1989
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      22.40

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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            9043
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.96
_reflns_number_total             1721
_reflns_number_gt                1169
_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^)+(0.0575P)^2^+0.4305P] 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    contra
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         1721
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
C1 C 0.18749(12) 2.2444(6) 0.13473(17) 0.0857(11) Uani 1 1 d . . .
H1 H 0.2049 2.3570 0.1361 0.103 Uiso 1 1 calc R . .
C2 C 0.18246(15) 2.1341(7) 0.17345(16) 0.0979(13) Uani 1 1 d . . .
H2 H 0.1964 2.1710 0.2017 0.117 Uiso 1 1 calc R . .
C3 C 0.16706(12) 2.1903(5) 0.09385(15) 0.0784(10) Uani 1 1 d . . .
H3 H 0.1705 2.2671 0.0672 0.094 Uiso 1 1 calc R . .
C4 C 0.15652(13) 1.9656(7) 0.17154(15) 0.0883(11) Uani 1 1 d . . .
H4 H 0.1532 1.8906 0.1985 0.106 Uiso 1 1 calc R . .
C5 C 0.14119(10) 2.0240(4) 0.09069(12) 0.0640(8) Uani 1 1 d . . .
H5 H 0.1275 1.9895 0.0621 0.077 Uiso 1 1 calc R . .
C6 C 0.13553(9) 1.9086(4) 0.12988(12) 0.0600(7) Uani 1 1 d . . .
C7 C 0.10907(11) 1.7334(5) 0.12696(13) 0.0674(8) Uani 1 1 d . . .
C8 C 0.08716(10) 1.5880(5) 0.12410(13) 0.0674(8) Uani 1 1 d . . .
C9 C 0.06138(9) 1.4136(4) 0.12402(12) 0.0601(7) Uani 1 1 d . . .
C10 C 0.04722(9) 1.3115(4) 0.16384(10) 0.0537(7) Uani 1 1 d . . .
C11 C 0.05892(12) 1.3714(5) 0.21308(11) 0.0672(9) Uani 1 1 d . . .
H11C H 0.0759 1.4903 0.2123 0.101 Uiso 1 1 calc R . .
H11B H 0.0778 1.2741 0.2278 0.101 Uiso 1 1 calc R . .
H11A H 0.0306 1.3883 0.2308 0.101 Uiso 1 1 calc R . .
C12 C 0.04597(10) 1.3120(5) 0.08375(12) 0.0655(8) Uani 1 1 d . . .
C13 C 0.05501(14) 1.3627(6) 0.03354(14) 0.0888(12) Uani 1 1 d . . .
H13C H 0.0406 1.2690 0.0133 0.133 Uiso 1 1 calc R . .
H13B H 0.0881 1.3645 0.0279 0.133 Uiso 1 1 calc R . .
H13A H 0.0422 1.4873 0.0269 0.133 Uiso 1 1 calc R . .
C14 C 0.02262(9) 1.1485(4) 0.14699(10) 0.0517(7) Uani 1 1 d . . .
C15 C 0.0000 1.0000 0.17097(13) 0.0475(9) Uani 1 2 d S . .
C16 C 0.0000 1.0000 0.22370(13) 0.0455(8) Uani 1 2 d S . .
C17 C 0.03685(10) 0.9203(4) 0.24799(11) 0.0575(7) Uani 1 1 d . . .
H17 H 0.0618 0.8662 0.2316 0.069 Uiso 1 1 calc R . .
C18 C 0.03665(13) 0.9210(5) 0.29723(13) 0.0744(10) Uani 1 1 d . . .
H18 H 0.0616 0.8675 0.3137 0.089 Uiso 1 1 calc R . .
C19 C 0.0000 1.0000 0.32160(19) 0.0810(14) Uani 1 2 d S . .
H19 H 0.0000 1.0000 0.3545 0.097 Uiso 1 2 calc SR . .
B1 B 0.0000 1.0000 0.06528(18) 0.0660(13) Uani 1 2 d S . .
N1 N 0.02265(8) 1.1530(4) 0.09741(9) 0.0589(6) Uani 1 1 d . . .
F1 F 0.03395(8) 0.9161(3) 0.03706(8) 0.0964(7) 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
C1 0.0737(19) 0.079(2) 0.105(3) -0.003(2) -0.007(2) -0.0113(19)
C2 0.094(2) 0.114(4) 0.086(3) -0.011(3) -0.023(2) -0.015(3)
C3 0.085(2) 0.062(2) 0.088(3) 0.0126(18) 0.0038(19) -0.0072(19)
C4 0.086(2) 0.109(3) 0.070(2) 0.018(2) -0.0010(19) -0.001(2)
C5 0.0694(16) 0.0576(18) 0.065(2) 0.0012(16) 0.0015(14) -0.0047(15)
C6 0.0541(13) 0.0592(17) 0.067(2) 0.0064(15) 0.0085(14) 0.0016(13)
C7 0.0651(15) 0.0657(19) 0.071(2) 0.0139(17) 0.0131(15) 0.0018(16)
C8 0.0631(14) 0.0587(18) 0.080(2) 0.0173(17) 0.0168(17) 0.0029(15)
C9 0.0601(13) 0.0558(16) 0.064(2) 0.0106(16) 0.0068(15) 0.0030(13)
C10 0.0543(13) 0.0511(16) 0.0556(17) 0.0027(14) 0.0073(13) 0.0025(13)
C11 0.0784(18) 0.0558(18) 0.068(2) -0.0015(15) 0.0009(16) -0.0160(15)
C12 0.0665(16) 0.0693(19) 0.0607(19) 0.0143(17) 0.0128(15) 0.0058(16)
C13 0.102(2) 0.098(3) 0.066(2) 0.025(2) 0.019(2) 0.000(2)
C14 0.0570(14) 0.0536(17) 0.0446(16) 0.0015(13) 0.0031(12) 0.0019(12)
C15 0.0483(16) 0.050(2) 0.044(2) 0.000 0.000 0.0007(16)
C16 0.0549(17) 0.0360(18) 0.045(2) 0.000 0.000 -0.0048(16)
C17 0.0618(15) 0.0484(15) 0.062(2) 0.0020(14) -0.0042(13) -0.0033(13)
C18 0.101(2) 0.059(2) 0.063(2) 0.0102(16) -0.029(2) -0.0062(18)
C19 0.128(4) 0.068(3) 0.047(3) 0.000 0.000 -0.012(3)
B1 0.075(3) 0.079(4) 0.043(3) 0.000 0.000 -0.003(3)
N1 0.0620(12) 0.0669(17) 0.0477(15) 0.0070(12) 0.0056(11) 0.0005(12)
F1 0.1111(14) 0.1159(17) 0.0621(12) -0.0194(12) 0.0279(12) -0.0105(13)

_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 1.345(6) . ?
C1 C3 1.350(5) . ?
C1 H1 0.9300 . ?
C2 C4 1.389(6) . ?
C2 H2 0.9300 . ?
C3 C5 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.381(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(5) . ?
C7 C8 1.193(4) . ?
C8 C9 1.420(4) . ?
C9 C10 1.392(4) . ?
C9 C12 1.411(5) . ?
C10 C14 1.418(4) . ?
C10 C11 1.492(4) . ?
C11 H11C 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11A 0.9600 . ?
C12 N1 1.349(4) . ?
C12 C13 1.486(5) . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13A 0.9600 . ?
C14 C15 1.395(3) . ?
C14 N1 1.403(3) . ?
C15 C14 1.395(3) 2_575 ?
C15 C16 1.492(5) . ?
C16 C17 1.376(3) . ?
C16 C17 1.376(3) 2_575 ?
C17 C18 1.393(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C18 1.370(5) 2_575 ?
C19 H19 0.9300 . ?
B1 F1 1.386(4) 2_575 ?
B1 F1 1.386(4) . ?
B1 N1 1.543(4) . ?
B1 N1 1.543(4) 2_575 ?

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 C3 119.5(4) . . ?
C2 C1 H1 120.3 . . ?
C3 C1 H1 120.3 . . ?
C1 C2 C4 120.5(4) . . ?
C1 C2 H2 119.8 . . ?
C4 C2 H2 119.8 . . ?
C1 C3 C5 121.6(4) . . ?
C1 C3 H3 119.2 . . ?
C5 C3 H3 119.2 . . ?
C6 C4 C2 120.6(4) . . ?
C6 C4 H4 119.7 . . ?
C2 C4 H4 119.7 . . ?
C3 C5 C6 120.0(3) . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C4 117.9(3) . . ?
C5 C6 C7 120.7(3) . . ?
C4 C6 C7 121.5(3) . . ?
C8 C7 C6 179.4(4) . . ?
C7 C8 C9 176.2(4) . . ?
C10 C9 C12 107.9(2) . . ?
C10 C9 C8 125.9(3) . . ?
C12 C9 C8 126.3(3) . . ?
C9 C10 C14 106.3(3) . . ?
C9 C10 C11 123.2(3) . . ?
C14 C10 C11 130.5(3) . . ?
C10 C11 H11C 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
N1 C12 C9 109.5(3) . . ?
N1 C12 C13 123.7(3) . . ?
C9 C12 C13 126.7(3) . . ?
C12 C13 H13C 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
C15 C14 N1 120.2(3) . . ?
C15 C14 C10 131.3(3) . . ?
N1 C14 C10 108.5(2) . . ?
C14 C15 C14 121.8(4) 2_575 . ?
C14 C15 C16 119.09(19) 2_575 . ?
C14 C15 C16 119.09(19) . . ?
C17 C16 C17 120.1(4) . 2_575 ?
C17 C16 C15 119.97(19) . . ?
C17 C16 C15 119.97(19) 2_575 . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C18 119.6(5) 2_575 . ?
C18 C19 H19 120.2 2_575 . ?
C18 C19 H19 120.2 . . ?
F1 B1 F1 109.7(4) 2_575 . ?
F1 B1 N1 110.08(14) 2_575 . ?
F1 B1 N1 109.59(13) . . ?
F1 B1 N1 109.59(13) 2_575 2_575 ?
F1 B1 N1 110.08(14) . 2_575 ?
N1 B1 N1 107.8(4) . 2_575 ?
C12 N1 C14 107.8(3) . . ?
C12 N1 B1 127.2(3) . . ?
C14 N1 B1 125.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.030