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


data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Zhong, Yihan'
'Si, Liping'
'He, Hongshan'
'Sykes, Andrew'

_publ_contact_author_name        'He, Hongshan'
_publ_contact_author_email       hongshan.he@sdstate.edu

_publ_section_title              
;
BODIPY chromophores as efficient green light sensitizers
for lanthanide-induced near-infrared emission
;

# Attachment '- 09051.cif'

data_09051
_database_code_depnum_ccdc_archive 'CCDC 830682'
#TrackingRef '- 09051.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Q-BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 B F2 N3 O, C H4 O'
_chemical_formula_sum            'C23 H24 B F2 N3 O2'
_chemical_formula_weight         423.26

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'
O O 0.0106 0.0060 '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'
B B 0.0013 0.0007 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3778(4)
_cell_length_b                   10.1815(5)
_cell_length_c                   13.4155(7)
_cell_angle_alpha                105.1200(10)
_cell_angle_beta                 97.6610(10)
_cell_angle_gamma                108.8840(10)
_cell_volume                     1015.12(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5840
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.46

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10017
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3554
_reflns_number_gt                2931
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2006)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2006)'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_molecular_graphics    'Ortep-3(Farrugia, 1997)'
_computing_publication_material  'WinGX(Farrugia, 1999)'

_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^)+(0.0931P)^2^+1.8748P] 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         3554
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.7991(4) 0.8878(3) 0.1252(2) 0.0156(6) Uani 1 1 d . . .
C2 C 0.6540(4) 0.9137(3) 0.1454(2) 0.0179(6) Uani 1 1 d . . .
H2 H 0.6137 0.9729 0.1126 0.021 Uiso 1 1 calc R . .
C3 C 0.5642(4) 0.8530(3) 0.2144(2) 0.0166(6) Uani 1 1 d . . .
H3 H 0.4639 0.8724 0.2273 0.020 Uiso 1 1 calc R . .
C4 C 0.6174(4) 0.7668(3) 0.2635(2) 0.0149(6) Uani 1 1 d . . .
C5 C 0.7667(4) 0.7361(3) 0.2428(2) 0.0152(6) Uani 1 1 d . . .
C6 C 0.8576(3) 0.7960(3) 0.1724(2) 0.0148(6) Uani 1 1 d . . .
C7 C 0.8295(4) 0.6459(3) 0.2880(2) 0.0174(6) Uani 1 1 d . . .
H7 H 0.7752 0.6060 0.3369 0.021 Uiso 1 1 calc R . .
C8 C 0.9691(4) 0.6166(3) 0.2607(2) 0.0194(6) Uani 1 1 d . . .
H8 H 1.0121 0.5556 0.2899 0.023 Uiso 1 1 calc R . .
C9 C 1.0479(4) 0.6785(3) 0.1886(2) 0.0189(6) Uani 1 1 d . . .
H9 H 1.1430 0.6555 0.1691 0.023 Uiso 1 1 calc R . .
C10 C 0.5204(3) 0.7042(3) 0.3368(2) 0.0149(6) Uani 1 1 d . . .
C11 C 0.3932(4) 0.5621(3) 0.2964(2) 0.0151(6) Uani 1 1 d . . .
C12 C 0.3334(4) 0.4555(3) 0.1933(2) 0.0170(6) Uani 1 1 d . . .
C13 C 0.3944(4) 0.4646(3) 0.0944(2) 0.0227(7) Uani 1 1 d . . .
H13A H 0.4856 0.5611 0.1092 0.034 Uiso 1 1 calc R . .
H13B H 0.2967 0.4508 0.0384 0.034 Uiso 1 1 calc R . .
H13C H 0.4407 0.3879 0.0708 0.034 Uiso 1 1 calc R . .
C14 C 0.2060(4) 0.3343(3) 0.2003(2) 0.0185(6) Uani 1 1 d . . .
H14 H 0.1420 0.2453 0.1438 0.022 Uiso 1 1 calc R . .
C15 C 0.1870(4) 0.3650(3) 0.3057(2) 0.0173(6) Uani 1 1 d . . .
C16 C 0.0650(4) 0.2681(3) 0.3511(3) 0.0230(7) Uani 1 1 d . . .
H16A H 0.0813 0.3192 0.4267 0.034 Uiso 1 1 calc R . .
H16B H 0.0882 0.1779 0.3430 0.034 Uiso 1 1 calc R . .
H16C H -0.0548 0.2433 0.3135 0.034 Uiso 1 1 calc R . .
N2 N 0.2993(3) 0.5015(2) 0.36311(18) 0.0150(5) Uani 1 1 d . . .
N3 N 0.4753(3) 0.7283(3) 0.51465(18) 0.0159(5) Uani 1 1 d . . .
C19 C 0.4824(4) 0.7994(3) 0.7081(2) 0.0220(7) Uani 1 1 d . . .
H19A H 0.3889 0.7025 0.6863 0.033 Uiso 1 1 calc R . .
H19B H 0.4389 0.8750 0.7399 0.033 Uiso 1 1 calc R . .
H19C H 0.5789 0.8032 0.7603 0.033 Uiso 1 1 calc R . .
C20 C 0.5445(4) 0.8260(3) 0.6129(2) 0.0180(6) Uani 1 1 d . . .
C21 C 0.6765(4) 0.9504(3) 0.6086(2) 0.0193(6) Uani 1 1 d . . .
H21 H 0.7463 1.0348 0.6676 0.023 Uiso 1 1 calc R . .
C22 C 0.6874(4) 0.9289(3) 0.5039(2) 0.0172(6) Uani 1 1 d . . .
C23 C 0.8090(4) 1.0388(3) 0.4655(2) 0.0205(6) Uani 1 1 d . . .
H23A H 0.7924 0.9981 0.3884 0.031 Uiso 1 1 calc R . .
H23B H 0.9292 1.0610 0.5009 0.031 Uiso 1 1 calc R . .
H23C H 0.7847 1.1290 0.4820 0.031 Uiso 1 1 calc R . .
N1 N 0.9976(3) 0.7664(3) 0.14651(18) 0.0174(5) Uani 1 1 d . . .
C18 C 0.5612(4) 0.7870(3) 0.4440(2) 0.0153(6) Uani 1 1 d . . .
O1 O 0.8928(3) 0.9424(2) 0.06079(16) 0.0201(5) Uani 1 1 d . . .
C17 C 1.2290(4) 0.7538(3) -0.0448(3) 0.0276(7) Uani 1 1 d . . .
H17A H 1.3020 0.7808 -0.0932 0.041 Uiso 1 1 calc R . .
H17B H 1.1123 0.6859 -0.0862 0.041 Uiso 1 1 calc R . .
H17C H 1.2800 0.7063 -0.0020 0.041 Uiso 1 1 calc R . .
O3 O 1.2185(3) 0.8827(2) 0.02361(17) 0.0225(5) Uani 1 1 d . . .
F1 F 0.1677(2) 0.61193(18) 0.49259(13) 0.0222(4) Uani 1 1 d . . .
F2 F 0.3397(2) 0.49719(18) 0.54358(13) 0.0225(4) Uani 1 1 d . . .
B1 B 0.3163(4) 0.5818(4) 0.4815(3) 0.0168(7) Uani 1 1 d . . .
H99 H 0.839(7) 1.001(6) 0.036(5) 0.087(18) Uiso 1 1 d . . .
H100 H 1.140(5) 0.855(4) 0.058(3) 0.037(11) 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
C1 0.0191(14) 0.0130(13) 0.0125(13) 0.0038(11) 0.0049(11) 0.0028(11)
C2 0.0223(15) 0.0161(14) 0.0184(14) 0.0094(11) 0.0057(12) 0.0078(12)
C3 0.0154(14) 0.0152(14) 0.0193(14) 0.0057(11) 0.0061(11) 0.0050(11)
C4 0.0162(14) 0.0134(13) 0.0126(13) 0.0032(11) 0.0035(11) 0.0033(11)
C5 0.0162(14) 0.0132(13) 0.0117(13) 0.0026(11) 0.0019(11) 0.0015(11)
C6 0.0140(13) 0.0140(13) 0.0119(13) 0.0018(11) 0.0018(10) 0.0020(11)
C7 0.0193(14) 0.0168(14) 0.0153(14) 0.0069(11) 0.0042(11) 0.0042(12)
C8 0.0215(15) 0.0183(14) 0.0201(15) 0.0076(12) 0.0030(12) 0.0090(12)
C9 0.0169(14) 0.0212(15) 0.0195(15) 0.0055(12) 0.0060(12) 0.0084(12)
C10 0.0147(14) 0.0174(14) 0.0172(14) 0.0090(11) 0.0059(11) 0.0083(11)
C11 0.0157(14) 0.0174(14) 0.0161(14) 0.0084(11) 0.0066(11) 0.0076(11)
C12 0.0177(14) 0.0194(14) 0.0173(14) 0.0080(12) 0.0054(11) 0.0091(12)
C13 0.0272(16) 0.0225(15) 0.0133(14) 0.0026(12) 0.0056(12) 0.0050(13)
C14 0.0160(14) 0.0164(14) 0.0188(14) 0.0017(11) 0.0018(11) 0.0047(12)
C15 0.0142(14) 0.0161(14) 0.0228(15) 0.0070(12) 0.0051(11) 0.0065(11)
C16 0.0215(15) 0.0184(15) 0.0300(17) 0.0094(13) 0.0113(13) 0.0056(13)
N2 0.0148(12) 0.0160(12) 0.0174(12) 0.0090(10) 0.0061(9) 0.0059(10)
N3 0.0192(12) 0.0175(12) 0.0142(12) 0.0066(10) 0.0063(9) 0.0088(10)
C19 0.0295(17) 0.0248(16) 0.0160(15) 0.0076(12) 0.0085(12) 0.0138(13)
C20 0.0201(15) 0.0218(15) 0.0166(14) 0.0077(12) 0.0053(11) 0.0120(12)
C21 0.0198(15) 0.0177(14) 0.0166(14) 0.0003(11) 0.0015(11) 0.0076(12)
C22 0.0172(14) 0.0173(14) 0.0187(15) 0.0057(12) 0.0037(11) 0.0090(12)
C23 0.0180(15) 0.0163(14) 0.0229(15) 0.0057(12) 0.0025(12) 0.0025(12)
N1 0.0172(12) 0.0165(12) 0.0168(12) 0.0045(10) 0.0046(10) 0.0046(10)
C18 0.0148(14) 0.0179(14) 0.0175(14) 0.0098(11) 0.0070(11) 0.0074(11)
O1 0.0225(11) 0.0247(11) 0.0215(11) 0.0150(9) 0.0124(9) 0.0107(9)
C17 0.0311(18) 0.0273(17) 0.0302(18) 0.0112(14) 0.0110(14) 0.0155(14)
O3 0.0258(12) 0.0236(11) 0.0257(12) 0.0133(9) 0.0147(10) 0.0114(9)
F1 0.0192(9) 0.0241(9) 0.0241(9) 0.0060(7) 0.0109(7) 0.0085(7)
F2 0.0288(10) 0.0225(9) 0.0200(9) 0.0129(7) 0.0092(7) 0.0083(8)
B1 0.0181(16) 0.0185(16) 0.0172(16) 0.0081(13) 0.0072(13) 0.0079(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 O1 1.350(3) . ?
C1 C2 1.370(4) . ?
C1 C6 1.428(4) . ?
C2 C3 1.411(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.428(4) . ?
C4 C10 1.496(4) . ?
C5 C7 1.416(4) . ?
C5 C6 1.426(4) . ?
C6 N1 1.368(4) . ?
C7 C8 1.368(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(4) . ?
C8 H8 0.9500 . ?
C9 N1 1.320(4) . ?
C9 H9 0.9500 . ?
C10 C18 1.395(4) . ?
C10 C11 1.400(4) . ?
C11 N2 1.401(3) . ?
C11 C12 1.423(4) . ?
C12 C14 1.381(4) . ?
C12 C13 1.498(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.408(4) . ?
C14 H14 0.9500 . ?
C15 N2 1.346(4) . ?
C15 C16 1.489(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 B1 1.548(4) . ?
N3 C20 1.343(4) . ?
N3 C18 1.404(3) . ?
N3 B1 1.552(4) . ?
C19 C20 1.496(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.407(4) . ?
C21 C22 1.385(4) . ?
C21 H21 0.9500 . ?
C22 C18 1.425(4) . ?
C22 C23 1.503(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 H99 0.95(6) . ?
C17 O3 1.429(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 H100 0.87(4) . ?
F1 B1 1.393(4) . ?
F2 B1 1.384(4) . ?

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
O1 C1 C2 124.2(3) . . ?
O1 C1 C6 116.0(2) . . ?
C2 C1 C6 119.8(2) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C10 120.9(2) . . ?
C5 C4 C10 120.2(2) . . ?
C7 C5 C6 117.3(3) . . ?
C7 C5 C4 123.1(2) . . ?
C6 C5 C4 119.6(2) . . ?
N1 C6 C5 122.4(3) . . ?
N1 C6 C1 118.4(2) . . ?
C5 C6 C1 119.3(3) . . ?
C8 C7 C5 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C5 C7 H7 120.2 . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N1 C9 C8 124.0(3) . . ?
N1 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C18 C10 C11 121.5(2) . . ?
C18 C10 C4 119.4(2) . . ?
C11 C10 C4 119.0(2) . . ?
N2 C11 C10 120.2(2) . . ?
N2 C11 C12 107.7(2) . . ?
C10 C11 C12 132.1(3) . . ?
C14 C12 C11 106.5(2) . . ?
C14 C12 C13 124.6(3) . . ?
C11 C12 C13 128.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 108.4(3) . . ?
C12 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
N2 C15 C14 108.9(2) . . ?
N2 C15 C16 123.2(3) . . ?
C14 C15 C16 127.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 N2 C11 108.5(2) . . ?
C15 N2 B1 126.1(2) . . ?
C11 N2 B1 125.3(2) . . ?
C20 N3 C18 108.4(2) . . ?
C20 N3 B1 126.4(2) . . ?
C18 N3 B1 124.9(2) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C21 109.2(2) . . ?
N3 C20 C19 122.7(3) . . ?
C21 C20 C19 128.1(3) . . ?
C22 C21 C20 108.4(3) . . ?
C22 C21 H21 125.8 . . ?
C20 C21 H21 125.8 . . ?
C21 C22 C18 106.3(2) . . ?
C21 C22 C23 124.8(3) . . ?
C18 C22 C23 128.9(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 C6 117.8(2) . . ?
C10 C18 N3 120.2(3) . . ?
C10 C18 C22 131.9(3) . . ?
N3 C18 C22 107.8(2) . . ?
C1 O1 H99 106(3) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 O3 H100 108(3) . . ?
F2 B1 F1 109.7(2) . . ?
F2 B1 N2 110.7(2) . . ?
F1 B1 N2 109.7(2) . . ?
F2 B1 N3 110.7(2) . . ?
F1 B1 N3 109.2(2) . . ?
N2 B1 N3 106.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.079

# Attachment '- 09053.cif'

data_09053
_database_code_depnum_ccdc_archive 'CCDC 830683'
#TrackingRef '- 09053.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 B F2'
_chemical_formula_sum            'C15 H15 B F2'
_chemical_formula_weight         244.08

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.6854(7)
_cell_length_b                   14.2972(14)
_cell_length_c                   11.4501(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.0770(10)
_cell_angle_gamma                90.00
_cell_volume                     1202.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5889
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.45

_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11441
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2104
_reflns_number_gt                1759
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2006)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2006)'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_molecular_graphics    'Ortep-3(Farrugia, 1997)'
_computing_publication_material  'WinGX(Farrugia, 1999)'

_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^)+(0.1224P)^2^+2.4202P] 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         2104
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.2039
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.7157(5) 0.2270(2) 0.8827(3) 0.0282(8) Uani 1 1 d . . .
H1A H 0.7413 0.2312 0.8040 0.042 Uiso 1 1 calc R . .
H1B H 0.5867 0.2123 0.8690 0.042 Uiso 1 1 calc R . .
H1C H 0.7906 0.1776 0.9322 0.042 Uiso 1 1 calc R . .
C2 C 0.7589(4) 0.3183(2) 0.9482(3) 0.0242(7) Uani 1 1 d . . .
C3 C 0.8838(4) 0.3351(2) 1.0633(3) 0.0254(7) Uani 1 1 d . . .
H3 H 0.9597 0.2898 1.1145 0.030 Uiso 1 1 calc R . .
C4 C 0.8767(4) 0.4305(2) 1.0890(3) 0.0229(7) Uani 1 1 d . . .
C5 C 0.9836(4) 0.4817(2) 1.2006(3) 0.0276(8) Uani 1 1 d . . .
H5A H 0.9498 0.5480 1.1930 0.041 Uiso 1 1 calc R . .
H5B H 1.1138 0.4754 1.2096 0.041 Uiso 1 1 calc R . .
H5C H 0.9573 0.4552 1.2726 0.041 Uiso 1 1 calc R . .
C6 C 0.7454(4) 0.4696(2) 0.9869(3) 0.0216(7) Uani 1 1 d . . .
C7 C 0.6763(4) 0.39939(18) 0.9017(2) 0.0099(6) Uani 1 1 d . . .
C8 C 0.6873(4) 0.5614(2) 0.9625(3) 0.0210(7) Uani 1 1 d . . .
H8 H 0.7349 0.6080 1.0225 0.025 Uiso 1 1 calc R . .
C9 C 0.5307(5) 0.7659(2) 0.8777(3) 0.0273(8) Uani 1 1 d . . .
H9A H 0.6186 0.7550 0.9580 0.041 Uiso 1 1 calc R . .
H9B H 0.4190 0.7927 0.8883 0.041 Uiso 1 1 calc R . .
H9C H 0.5828 0.8093 0.8309 0.041 Uiso 1 1 calc R . .
C10 C 0.4876(4) 0.6755(2) 0.8107(3) 0.0227(7) Uani 1 1 d . . .
C11 C 0.3705(4) 0.6605(2) 0.6946(3) 0.0246(7) Uani 1 1 d . . .
H11 H 0.2999 0.7071 0.6426 0.030 Uiso 1 1 calc R . .
C12 C 0.3733(4) 0.5651(2) 0.6666(3) 0.0235(7) Uani 1 1 d . . .
C13 C 0.2697(5) 0.5160(2) 0.5527(3) 0.0272(8) Uani 1 1 d . . .
H13A H 0.1947 0.5613 0.4954 0.041 Uiso 1 1 calc R . .
H13B H 0.1911 0.4683 0.5725 0.041 Uiso 1 1 calc R . .
H13C H 0.3550 0.4860 0.5154 0.041 Uiso 1 1 calc R . .
C14 C 0.4891(3) 0.52006(19) 0.7630(2) 0.0105(6) Uani 1 1 d . . .
C15 C 0.5624(4) 0.5868(2) 0.8538(3) 0.0212(7) Uani 1 1 d . . .
F1 F 0.3708(2) 0.36448(13) 0.77591(17) 0.0276(5) Uani 1 1 d . . .
F2 F 0.5909(3) 0.38100(13) 0.68195(16) 0.0285(5) Uani 1 1 d . . .
B1 B 0.5292(5) 0.4134(3) 0.7767(3) 0.0209(8) 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 0.0349(19) 0.0221(17) 0.0277(17) 0.0005(13) 0.0093(14) 0.0010(14)
C2 0.0256(17) 0.0253(17) 0.0245(16) 0.0014(13) 0.0117(13) -0.0022(13)
C3 0.0256(17) 0.0244(17) 0.0253(17) 0.0042(13) 0.0062(13) 0.0022(13)
C4 0.0216(16) 0.0265(17) 0.0217(16) 0.0029(13) 0.0080(13) -0.0022(13)
C5 0.0245(17) 0.0310(18) 0.0249(17) 0.0005(14) 0.0034(14) -0.0017(14)
C6 0.0207(16) 0.0237(16) 0.0219(16) -0.0012(12) 0.0085(13) -0.0048(12)
C7 0.0109(13) 0.0087(13) 0.0108(13) 0.0008(10) 0.0042(10) -0.0015(10)
C8 0.0210(16) 0.0227(16) 0.0212(16) -0.0016(13) 0.0088(13) -0.0043(12)
C9 0.0264(17) 0.0233(17) 0.0310(18) -0.0007(14) 0.0064(14) -0.0003(13)
C10 0.0200(16) 0.0242(17) 0.0248(16) 0.0015(13) 0.0080(13) -0.0017(12)
C11 0.0222(16) 0.0241(17) 0.0261(17) 0.0049(14) 0.0046(13) 0.0006(13)
C12 0.0188(15) 0.0270(17) 0.0248(17) 0.0024(13) 0.0067(13) -0.0028(12)
C13 0.0271(17) 0.0289(18) 0.0234(17) 0.0001(14) 0.0040(14) -0.0024(14)
C14 0.0087(12) 0.0122(14) 0.0103(13) -0.0002(10) 0.0023(10) -0.0018(10)
C15 0.0197(15) 0.0225(16) 0.0230(16) -0.0021(13) 0.0090(13) -0.0029(12)
F1 0.0251(10) 0.0245(10) 0.0309(11) -0.0009(8) 0.0047(8) -0.0074(8)
F2 0.0357(12) 0.0275(10) 0.0231(10) -0.0011(8) 0.0097(8) 0.0057(8)
B1 0.0216(18) 0.0218(18) 0.0190(18) 0.0001(14) 0.0053(14) -0.0013(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
C1 C2 1.494(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.354(4) . ?
C2 C3 1.404(5) . ?
C3 C4 1.399(5) . ?
C3 H3 0.9500 . ?
C4 C6 1.416(4) . ?
C4 C5 1.492(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.387(5) . ?
C6 C7 1.392(4) . ?
C7 B1 1.555(4) . ?
C8 C15 1.379(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.490(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.386(5) . ?
C10 C15 1.420(4) . ?
C11 C12 1.402(5) . ?
C11 H11 0.9500 . ?
C12 C14 1.360(4) . ?
C12 C13 1.489(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.401(4) . ?
C14 B1 1.555(4) . ?
F1 B1 1.401(4) . ?
F2 B1 1.385(4) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 109.6(3) . . ?
C7 C2 C1 122.8(3) . . ?
C3 C2 C1 127.7(3) . . ?
C4 C3 C2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C3 C4 C6 105.9(3) . . ?
C3 C4 C5 127.8(3) . . ?
C6 C4 C5 126.4(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 120.5(3) . . ?
C8 C6 C4 130.4(3) . . ?
C7 C6 C4 109.0(3) . . ?
C2 C7 C6 107.7(3) . . ?
C2 C7 B1 127.1(3) . . ?
C6 C7 B1 125.2(3) . . ?
C15 C8 C6 121.9(3) . . ?
C15 C8 H8 119.1 . . ?
C6 C8 H8 119.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 106.2(3) . . ?
C11 C10 C9 127.7(3) . . ?
C15 C10 C9 126.1(3) . . ?
C10 C11 C12 108.7(3) . . ?
C10 C11 H11 125.7 . . ?
C12 C11 H11 125.7 . . ?
C14 C12 C11 109.0(3) . . ?
C14 C12 C13 122.8(3) . . ?
C11 C12 C13 128.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 107.7(3) . . ?
C12 C14 B1 127.6(3) . . ?
C15 C14 B1 124.6(3) . . ?
C8 C15 C14 120.8(3) . . ?
C8 C15 C10 130.7(3) . . ?
C14 C15 C10 108.4(3) . . ?
F2 B1 F1 109.0(3) . . ?
F2 B1 C7 110.7(3) . . ?
F1 B1 C7 109.7(3) . . ?
F2 B1 C14 110.6(3) . . ?
F1 B1 C14 110.0(3) . . ?
C7 B1 C14 106.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.089