# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global2
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#TrackingRef 'a.cif'

#============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name        'Prof. Zhen Shen'
_publ_contact_author_address     
;
Coordination Chemistry Institute and the State
Key Laboratory of Coordination Chemistry,
Nanjing University,
Nanjing 210093, P. R.China
;
_publ_contact_author_email       zshen@nju.edu.cn
_publ_contact_author_fax         '86 25 83314502'
_publ_contact_author_phone       '86 25 83686679'
_publ_contact_letter             
;
Please assign the CCDC number for this data and
inform me to the email: zshen@nju.edu.cn
Thanks a lot for your kind help.
;
#============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Specific Cu2+- induced J?aggregation and Hg2+-induced
fluorescence enhancement based on BODIPY
;
loop_
_publ_author_name
_publ_author_address
'Hanzhuang Liu'
; State Key Laboratory of Coordination Chemistry,
Nanjing National Laboratory of Microstructures,
Nanjing University,
Nanjing 210093, P. R.China
;
'Zhen Shen'
; State Key Laboratory of Coordination Chemistry,
Nanjing National Laboratory of Microstructures,
Nanjing University,
Nanjing 210093, P. R.China
;

#============================================================================
data_a
_database_code_depnum_ccdc_archive 'CCDC 843443'
#TrackingRef 'a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 B F2 N7'
_chemical_formula_weight         561.44

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   19.167(5)
_cell_length_b                   12.636(3)
_cell_length_c                   11.550(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2797.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            16633
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         28.37
_reflns_number_total             3474
_reflns_number_gt                1784
_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^)+(0.0679P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_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
F1 F 0.04862(4) 0.23727(6) 0.19383(7) 0.0600(3) Uani 1 1 d . . .
N2 N 0.03645(6) 0.37249(8) 0.34135(9) 0.0459(3) Uani 1 1 d . . .
N3 N 0.14498(6) 0.45526(9) 0.57636(9) 0.0572(4) Uani 1 1 d . . .
C4 C 0.03654(7) 0.48237(10) 0.32750(11) 0.0489(4) Uani 1 1 d . . .
C5 C 0.07885(8) 0.52606(11) 0.41696(11) 0.0519(4) Uani 1 1 d . . .
C6 C 0.10082(7) 0.44237(10) 0.48569(12) 0.0503(4) Uani 1 1 d . . .
N7 N 0.0000 0.53481(12) 0.2500 0.0518(5) Uani 1 2 d S . .
N8 N 0.09886(7) 0.62693(9) 0.43375(10) 0.0626(4) Uani 1 1 d . . .
C9 C 0.07213(7) 0.34589(10) 0.43819(11) 0.0474(4) Uani 1 1 d . . .
C10 C 0.07594(8) 0.23547(11) 0.61187(15) 0.0617(5) Uani 1 1 d . . .
H10 H 0.0718 0.2972 0.6552 0.074 Uiso 1 1 calc R . .
C11 C 0.07828(7) 0.24146(10) 0.49182(14) 0.0483(4) Uani 1 1 d . . .
C12 C 0.14294(9) 0.63969(12) 0.52103(13) 0.0636(5) Uani 1 1 d . . .
B13 B 0.0000 0.29849(17) 0.2500 0.0466(6) Uani 1 2 d S . .
C14 C 0.16590(8) 0.55381(12) 0.59326(12) 0.0606(5) Uani 1 1 d . . .
C15 C 0.08622(9) 0.14843(11) 0.42895(15) 0.0661(5) Uani 1 1 d . . .
H15 H 0.0886 0.1506 0.3486 0.079 Uiso 1 1 calc R . .
C16 C 0.21520(9) 0.57299(14) 0.69162(14) 0.0772(5) Uani 1 1 d . . .
H16A H 0.1917 0.6161 0.7491 0.093 Uiso 1 1 calc R . .
H16B H 0.2546 0.6134 0.6629 0.093 Uiso 1 1 calc R . .
C17 C 0.07973(9) 0.13969(13) 0.66725(14) 0.0725(5) Uani 1 1 d . . .
H17 H 0.0777 0.1366 0.7476 0.087 Uiso 1 1 calc R . .
C18 C 0.16939(10) 0.75182(14) 0.53260(17) 0.0953(6) Uani 1 1 d . . .
H18 H 0.1522 0.7993 0.5872 0.114 Uiso 1 1 calc R . .
C19 C 0.08654(10) 0.04769(13) 0.60340(16) 0.0792(6) Uani 1 1 d . . .
H19 H 0.0884 -0.0175 0.6406 0.095 Uiso 1 1 calc R . .
C20 C 0.09049(10) 0.05299(12) 0.48630(17) 0.0806(6) Uani 1 1 d . . .
H20 H 0.0962 -0.0090 0.4439 0.097 Uiso 1 1 calc R . .
C21 C 0.24255(9) 0.47438(14) 0.75036(18) 0.0859(6) Uani 1 1 d . . .
H21A H 0.2041 0.4326 0.7774 0.129 Uiso 1 1 calc R . .
H21B H 0.2714 0.4941 0.8148 0.129 Uiso 1 1 calc R . .
H21C H 0.2695 0.4339 0.6961 0.129 Uiso 1 1 calc R . .
C22 C 0.22327(13) 0.77823(18) 0.4519(2) 0.1327(9) Uani 1 1 d . . .
H22A H 0.2628 0.7330 0.4643 0.199 Uiso 1 1 calc R . .
H22B H 0.2369 0.8507 0.4628 0.199 Uiso 1 1 calc R . .
H22C H 0.2063 0.7688 0.3744 0.199 Uiso 1 1 calc R . .
H3 H 0.1835(9) 0.7445(13) 0.6151(16) 0.102(6) Uiso 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
F1 0.0674(5) 0.0519(5) 0.0608(5) -0.0071(4) 0.0008(4) 0.0165(4)
N2 0.0515(6) 0.0368(6) 0.0494(6) -0.0015(5) 0.0033(5) -0.0034(5)
N3 0.0555(7) 0.0565(8) 0.0595(7) -0.0087(6) 0.0062(6) -0.0121(6)
C4 0.0578(8) 0.0366(7) 0.0521(8) -0.0016(6) 0.0126(7) -0.0037(6)
C5 0.0617(9) 0.0402(8) 0.0538(8) -0.0060(7) 0.0142(7) -0.0085(7)
C6 0.0532(8) 0.0462(8) 0.0514(8) -0.0082(7) 0.0074(7) -0.0097(7)
N7 0.0670(10) 0.0398(9) 0.0486(9) 0.000 0.0109(8) 0.000
N8 0.0829(9) 0.0447(7) 0.0602(7) -0.0097(6) 0.0173(7) -0.0173(6)
C9 0.0450(8) 0.0452(8) 0.0522(8) -0.0043(6) 0.0043(7) -0.0048(6)
C10 0.0624(9) 0.0548(9) 0.0680(10) 0.0038(8) -0.0029(8) 0.0005(7)
C11 0.0445(7) 0.0428(8) 0.0576(9) 0.0005(6) -0.0054(7) -0.0047(6)
C12 0.0779(10) 0.0569(9) 0.0561(9) -0.0095(8) 0.0179(8) -0.0220(8)
B13 0.0536(13) 0.0372(11) 0.0491(13) 0.000 0.0074(11) 0.000
C14 0.0609(9) 0.0634(10) 0.0576(9) -0.0191(8) 0.0144(7) -0.0201(7)
C15 0.0805(11) 0.0467(9) 0.0711(10) -0.0002(8) -0.0178(9) 0.0045(8)
C16 0.0725(10) 0.0819(11) 0.0773(11) -0.0201(10) 0.0038(9) -0.0239(9)
C17 0.0731(11) 0.0752(11) 0.0693(11) 0.0186(9) -0.0030(9) 0.0032(9)
C18 0.1313(15) 0.0777(11) 0.0770(11) -0.0360(9) 0.0357(11) -0.0592(10)
C19 0.0837(12) 0.0533(10) 0.1005(13) 0.0232(9) -0.0230(10) -0.0038(9)
C20 0.1054(14) 0.0462(10) 0.0901(12) 0.0000(9) -0.0303(11) 0.0049(9)
C21 0.0724(11) 0.1000(13) 0.0854(12) -0.0165(11) -0.0108(10) -0.0144(10)
C22 0.172(2) 0.1093(16) 0.1162(18) -0.0130(13) 0.0293(16) -0.0816(14)

_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
F1 B13 1.3740(14) . ?
N2 C9 1.3534(17) . ?
N2 C4 1.3976(16) . ?
N2 B13 1.5734(16) . ?
N3 C14 1.3228(19) . ?
N3 C6 1.3563(18) . ?
C4 N7 1.3156(15) . ?
C4 C5 1.4249(19) . ?
C5 N8 1.3451(17) . ?
C5 C6 1.3877(19) . ?
C6 C9 1.4456(19) . ?
N7 C4 1.3156(15) 3 ?
N8 C12 1.325(2) . ?
C9 C11 1.4625(19) . ?
C10 C17 1.371(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C11 C15 1.390(2) . ?
C12 C14 1.438(2) . ?
C12 C18 1.511(2) . ?
B13 F1 1.3740(14) 3 ?
B13 N2 1.5734(16) 3 ?
C14 C16 1.497(2) . ?
C15 C20 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C21 1.513(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.383(2) . ?
C17 H17 0.9300 . ?
C18 C22 1.431(3) . ?
C18 H18 0.9300 . ?
C18 H3 0.995(19) . ?
C19 C20 1.356(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C9 N2 C4 109.92(10) . . ?
C9 N2 B13 129.12(11) . . ?
C4 N2 B13 120.94(11) . . ?
C14 N3 C6 114.59(12) . . ?
N7 C4 N2 125.28(12) . . ?
N7 C4 C5 126.95(12) . . ?
N2 C4 C5 107.62(11) . . ?
N8 C5 C6 123.58(13) . . ?
N8 C5 C4 129.35(13) . . ?
C6 C5 C4 106.99(12) . . ?
N3 C6 C5 122.65(12) . . ?
N3 C6 C9 129.17(13) . . ?
C5 C6 C9 108.07(13) . . ?
C4 N7 C4 119.51(16) 3 . ?
C12 N8 C5 114.00(13) . . ?
N2 C9 C6 107.24(11) . . ?
N2 C9 C11 127.94(12) . . ?
C6 C9 C11 124.72(13) . . ?
C17 C10 C11 120.80(14) . . ?
C17 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C15 118.60(13) . . ?
C10 C11 C9 117.98(12) . . ?
C15 C11 C9 123.41(14) . . ?
N8 C12 C14 123.00(13) . . ?
N8 C12 C18 113.29(14) . . ?
C14 C12 C18 123.63(15) . . ?
F1 B13 F1 111.46(16) 3 . ?
F1 B13 N2 108.61(5) 3 . ?
F1 B13 N2 110.49(6) . . ?
F1 B13 N2 110.49(6) 3 3 ?
F1 B13 N2 108.61(5) . 3 ?
N2 B13 N2 107.08(15) . 3 ?
N3 C14 C12 122.15(14) . . ?
N3 C14 C16 117.11(14) . . ?
C12 C14 C16 120.74(14) . . ?
C20 C15 C11 119.70(16) . . ?
C20 C15 H15 120.2 . . ?
C11 C15 H15 120.2 . . ?
C14 C16 C21 115.19(14) . . ?
C14 C16 H16A 108.5 . . ?
C21 C16 H16A 108.5 . . ?
C14 C16 H16B 108.5 . . ?
C21 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C10 C17 C19 119.89(16) . . ?
C10 C17 H17 120.1 . . ?
C19 C17 H17 120.1 . . ?
C22 C18 C12 113.78(16) . . ?
C22 C18 H18 123.1 . . ?
C12 C18 H18 123.1 . . ?
C22 C18 H3 116.7(11) . . ?
C12 C18 H3 95.1(10) . . ?
H18 C18 H3 60.5 . . ?
C20 C19 C17 119.71(15) . . ?
C20 C19 H19 120.1 . . ?
C17 C19 H19 120.1 . . ?
C19 C20 C15 121.27(16) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045