# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        F.Gabbai
_publ_contact_author_email       FRANCOIS@TAMU.EDU

_publ_section_title              
;
Colorimetric turn-on sensing of fluoride ions
in H2O/CHCl3 mixtures by pyridinium boranes
;
loop_
_publ_author_name
'F Gabbai'
'Casey R Wade'

# Attachment '3F-sorted.cif'

data_n
_database_code_depnum_ccdc_archive 'CCDC 738717'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32.24 H36.71 B F N1.76 O0.24'
_chemical_formula_weight         482.51

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.924(3)
_cell_length_b                   12.520(3)
_cell_length_c                   15.974(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.333(3)
_cell_angle_gamma                90.00
_cell_volume                     2730.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      4.414
_cell_measurement_theta_max      46.217

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1034
_exptl_absorpt_coefficient_mu    0.072
_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      110(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            22904
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         24.00
_reflns_number_total             4278
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEX
_computing_cell_refinement       APEX
_computing_data_reduction        APEX
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
The residual electron density found in the lattice could be satisfactorily
modeled on the basis of an acetone and an acetonitrile molecule which were
refined in split positions with complementary occupancies.
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^)+(0.0690P)^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         4278
_refine_ls_number_parameters     351
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.000
_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
F1 F 0.61097(11) -0.29297(12) 0.16647(9) 0.0276(4) Uani 1 1 d . . .
N1 N 0.42109(16) -0.03670(18) -0.23547(14) 0.0260(6) Uani 1 1 d . . .
N2 N 1.2377(5) -0.0938(5) 0.1482(4) 0.0722(17) Uani 0.791(6) 1 d P A 2
O1 O 1.1787(16) -0.1300(11) 0.1032(12) 0.065(5) Uani 0.209(6) 1 d PD A 1
B1 B 0.6772(2) -0.2799(3) 0.1050(2) 0.0249(8) Uani 1 1 d . . .
C1 C 0.3713(2) 0.0055(2) -0.30933(19) 0.0315(7) Uani 1 1 d . . .
H1A H 0.3684 0.0793 -0.3156 0.038 Uiso 1 1 calc R . .
C2 C 0.3251(2) -0.0574(2) -0.37495(19) 0.0335(8) Uani 1 1 d . . .
H2A H 0.2921 -0.0273 -0.4258 0.040 Uiso 1 1 calc R . .
C3 C 0.3285(2) -0.1669(2) -0.36380(19) 0.0353(8) Uani 1 1 d . . .
H3A H 0.2976 -0.2118 -0.4072 0.042 Uiso 1 1 calc R . .
C4 C 0.3781(2) -0.2091(2) -0.28782(18) 0.0314(8) Uani 1 1 d . . .
H4A H 0.3795 -0.2828 -0.2802 0.038 Uiso 1 1 calc R . .
C5 C 0.42570(19) -0.1444(2) -0.22275(18) 0.0244(7) Uani 1 1 d . . .
C6 C 0.4840(2) -0.1857(2) -0.14172(17) 0.0241(7) Uani 1 1 d . . .
C7 C 0.5765(2) -0.2287(2) -0.14160(18) 0.0258(7) Uani 1 1 d . . .
H7A H 0.5994 -0.2343 -0.1923 0.031 Uiso 1 1 calc R . .
C8 C 0.6339(2) -0.2629(2) -0.06574(17) 0.0265(7) Uani 1 1 d . . .
H8A H 0.6945 -0.2933 -0.0672 0.032 Uiso 1 1 calc R . .
C9 C 0.60510(19) -0.25391(19) 0.01356(17) 0.0222(7) Uani 1 1 d . . .
C10 C 0.5087(2) -0.2184(2) 0.00941(18) 0.0260(7) Uani 1 1 d . . .
H10A H 0.4836 -0.2177 0.0592 0.031 Uiso 1 1 calc R . .
C11 C 0.4493(2) -0.1842(2) -0.06582(18) 0.0265(7) Uani 1 1 d . . .
H11A H 0.3861 -0.1602 -0.0656 0.032 Uiso 1 1 calc R . .
C12 C 0.7471(2) -0.1779(2) 0.14997(18) 0.0268(7) Uani 1 1 d . . .
C13 C 0.7986(2) -0.1920(2) 0.23574(19) 0.0285(7) Uani 1 1 d . . .
C14 C 0.8094(2) -0.3008(2) 0.27881(18) 0.0336(8) Uani 1 1 d . . .
H14A H 0.8462 -0.2935 0.3360 0.050 Uiso 1 1 calc R . .
H14B H 0.8431 -0.3483 0.2473 0.050 Uiso 1 1 calc R . .
H14C H 0.7457 -0.3291 0.2804 0.050 Uiso 1 1 calc R . .
C15 C 0.8451(2) -0.1065(2) 0.28362(19) 0.0330(8) Uani 1 1 d . . .
H15A H 0.8763 -0.1186 0.3398 0.040 Uiso 1 1 calc R . .
C16 C 0.8462(2) -0.0045(2) 0.2503(2) 0.0346(8) Uani 1 1 d . . .
C17 C 0.8956(2) 0.0885(2) 0.3026(2) 0.0458(9) Uani 1 1 d . . .
H17A H 0.8882 0.1519 0.2682 0.069 Uiso 1 1 calc R . .
H17B H 0.9639 0.0732 0.3216 0.069 Uiso 1 1 calc R . .
H17C H 0.8657 0.0994 0.3513 0.069 Uiso 1 1 calc R . .
C18 C 0.8009(2) 0.0086(2) 0.1661(2) 0.0337(8) Uani 1 1 d . . .
H18A H 0.8022 0.0759 0.1417 0.040 Uiso 1 1 calc R . .
C19 C 0.7532(2) -0.0739(2) 0.11544(18) 0.0272(7) Uani 1 1 d . . .
C20 C 0.7130(2) -0.0453(2) 0.02298(18) 0.0330(8) Uani 1 1 d . . .
H20A H 0.7252 0.0289 0.0139 0.049 Uiso 1 1 calc R . .
H20B H 0.6438 -0.0584 0.0099 0.049 Uiso 1 1 calc R . .
H20C H 0.7447 -0.0881 -0.0135 0.049 Uiso 1 1 calc R . .
C21 C 0.73482(19) -0.3930(2) 0.09533(17) 0.0251(7) Uani 1 1 d . . .
C22 C 0.6901(2) -0.4935(2) 0.10531(17) 0.0268(7) Uani 1 1 d . . .
C23 C 0.5874(2) -0.5025(2) 0.1234(2) 0.0377(8) Uani 1 1 d . . .
H23A H 0.5709 -0.5765 0.1279 0.057 Uiso 1 1 calc R . .
H23B H 0.5416 -0.4700 0.0777 0.057 Uiso 1 1 calc R . .
H23C H 0.5847 -0.4668 0.1761 0.057 Uiso 1 1 calc R . .
C24 C 0.7388(2) -0.5889(2) 0.09684(18) 0.0304(7) Uani 1 1 d . . .
H24A H 0.7084 -0.6529 0.1056 0.036 Uiso 1 1 calc R . .
C25 C 0.8305(2) -0.5924(2) 0.07601(18) 0.0305(7) Uani 1 1 d . . .
C26 C 0.8820(2) -0.6977(2) 0.0671(2) 0.0430(9) Uani 1 1 d . . .
H26A H 0.8417 -0.7557 0.0790 0.065 Uiso 1 1 calc R . .
H26B H 0.9435 -0.6993 0.1067 0.065 Uiso 1 1 calc R . .
H26C H 0.8932 -0.7044 0.0099 0.065 Uiso 1 1 calc R . .
C27 C 0.8726(2) -0.4953(2) 0.06223(18) 0.0292(7) Uani 1 1 d . . .
H27A H 0.9332 -0.4952 0.0460 0.035 Uiso 1 1 calc R . .
C28 C 0.82774(19) -0.3978(2) 0.07174(17) 0.0248(7) Uani 1 1 d . . .
C29 C 0.8839(2) -0.2986(2) 0.05634(19) 0.0316(7) Uani 1 1 d . . .
H29A H 0.9447 -0.3189 0.0411 0.047 Uiso 1 1 calc R . .
H29B H 0.8969 -0.2562 0.1074 0.047 Uiso 1 1 calc R . .
H29C H 0.8457 -0.2577 0.0108 0.047 Uiso 1 1 calc R . .
C30 C 0.4742(2) 0.0368(2) -0.17012(18) 0.0323(8) Uani 1 1 d . . .
H30A H 0.4629 0.1092 -0.1894 0.049 Uiso 1 1 calc R . .
H30B H 0.5431 0.0216 -0.1607 0.049 Uiso 1 1 calc R . .
H30C H 0.4512 0.0275 -0.1178 0.049 Uiso 1 1 calc R . .
C31 C 1.0757(9) -0.0748(13) 0.1995(6) 0.055(2) Uani 0.791(6) 1 d P A 2
H31A H 1.0898 -0.0472 0.2566 0.083 Uiso 0.791(6) 1 calc PR A 2
H31B H 1.0449 -0.1435 0.1993 0.083 Uiso 0.791(6) 1 calc PR A 2
H31C H 1.0326 -0.0267 0.1633 0.083 Uiso 0.791(6) 1 calc PR A 2
C32 C 1.1640(5) -0.0853(4) 0.1689(3) 0.0507(15) Uani 0.791(6) 1 d P A 2
C33 C 1.1043(16) -0.0861(17) 0.1123(18) 0.084(6) Uani 0.209(6) 1 d PD A 1
C34 C 1.0378(14) -0.0248(15) 0.0452(13) 0.084(6) Uani 0.209(6) 1 d PD . 1
H34A H 1.0603 -0.0300 -0.0077 0.126 Uiso 0.209(6) 1 d PR A 1
H34B H 0.9727 -0.0533 0.0380 0.126 Uiso 0.209(6) 1 d PR A 1
H34C H 1.0373 0.0488 0.0620 0.126 Uiso 0.209(6) 1 d PR A 1
C35 C 1.062(5) -0.070(6) 0.189(3) 0.084(6) Uani 0.209(6) 1 d PD A 1
H35A H 1.0991 -0.1072 0.2372 0.126 Uiso 0.209(6) 1 d PR A 1
H35B H 1.0604 0.0046 0.2013 0.126 Uiso 0.209(6) 1 d PR A 1
H35C H 0.9958 -0.0975 0.1772 0.126 Uiso 0.209(6) 1 d PR A 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
F1 0.0278(9) 0.0297(9) 0.0272(9) -0.0002(7) 0.0099(7) 0.0008(7)
N1 0.0257(14) 0.0251(14) 0.0267(15) 0.0014(11) 0.0040(12) -0.0013(11)
N2 0.097(4) 0.065(4) 0.063(4) 0.027(3) 0.036(4) 0.035(4)
O1 0.084(13) 0.047(9) 0.076(13) -0.003(8) 0.047(10) 0.003(9)
B1 0.0255(19) 0.0272(19) 0.0247(19) 0.0011(15) 0.0110(16) -0.0010(15)
C1 0.0293(17) 0.0303(18) 0.0359(19) 0.0086(16) 0.0085(15) 0.0040(15)
C2 0.0293(18) 0.042(2) 0.0281(19) 0.0042(16) 0.0039(15) 0.0034(15)
C3 0.0336(19) 0.038(2) 0.033(2) -0.0068(15) 0.0032(16) 0.0020(15)
C4 0.0350(19) 0.0246(17) 0.0335(19) -0.0016(14) 0.0039(15) 0.0049(14)
C5 0.0240(16) 0.0233(17) 0.0283(18) 0.0007(14) 0.0105(14) 0.0020(13)
C6 0.0266(17) 0.0180(15) 0.0268(17) 0.0004(13) 0.0034(14) -0.0012(13)
C7 0.0309(17) 0.0212(16) 0.0267(18) -0.0033(13) 0.0090(14) -0.0017(13)
C8 0.0245(17) 0.0237(16) 0.0320(19) 0.0000(14) 0.0075(14) 0.0023(13)
C9 0.0249(17) 0.0141(15) 0.0286(17) -0.0027(12) 0.0078(13) -0.0032(12)
C10 0.0295(17) 0.0236(16) 0.0256(18) -0.0016(13) 0.0073(14) -0.0022(14)
C11 0.0256(16) 0.0232(17) 0.0321(18) -0.0041(14) 0.0087(15) 0.0008(13)
C12 0.0225(16) 0.0297(18) 0.0292(18) -0.0014(14) 0.0076(14) 0.0024(13)
C13 0.0227(16) 0.0290(18) 0.0350(19) -0.0038(14) 0.0088(14) 0.0023(14)
C14 0.0374(19) 0.0348(19) 0.0273(18) -0.0004(14) 0.0034(15) 0.0035(15)
C15 0.0252(17) 0.036(2) 0.0348(19) -0.0048(16) -0.0010(14) 0.0037(15)
C16 0.0244(17) 0.0359(19) 0.043(2) -0.0112(16) 0.0061(15) -0.0022(15)
C17 0.037(2) 0.042(2) 0.055(2) -0.0146(17) 0.0006(17) -0.0066(17)
C18 0.0268(17) 0.0293(18) 0.045(2) -0.0023(16) 0.0065(15) -0.0023(14)
C19 0.0234(16) 0.0259(17) 0.0331(18) -0.0008(14) 0.0076(14) 0.0004(13)
C20 0.0354(18) 0.0247(16) 0.040(2) 0.0007(14) 0.0097(16) -0.0033(14)
C21 0.0241(17) 0.0289(17) 0.0207(16) 0.0013(13) 0.0004(13) -0.0010(13)
C22 0.0251(16) 0.0288(17) 0.0268(17) 0.0003(14) 0.0060(13) -0.0025(14)
C23 0.0344(19) 0.0321(18) 0.051(2) -0.0007(16) 0.0179(16) -0.0039(15)
C24 0.0325(18) 0.0243(17) 0.0340(18) 0.0044(14) 0.0059(15) -0.0028(14)
C25 0.0297(18) 0.0285(18) 0.0330(18) 0.0010(14) 0.0051(15) 0.0059(14)
C26 0.042(2) 0.0304(19) 0.059(2) -0.0011(16) 0.0167(18) 0.0043(16)
C27 0.0224(16) 0.0345(19) 0.0320(18) 0.0004(14) 0.0083(13) 0.0014(15)
C28 0.0221(16) 0.0260(17) 0.0254(17) 0.0014(13) 0.0027(13) -0.0010(13)
C29 0.0280(17) 0.0302(17) 0.0388(19) 0.0008(14) 0.0120(15) -0.0010(14)
C30 0.0360(18) 0.0244(16) 0.0361(19) -0.0001(14) 0.0058(15) -0.0034(14)
C31 0.053(5) 0.058(4) 0.056(4) -0.012(4) 0.014(4) -0.006(4)
C32 0.069(4) 0.038(3) 0.049(3) 0.007(2) 0.023(3) 0.017(3)
C33 0.081(13) 0.068(11) 0.099(14) 0.014(9) 0.008(10) -0.004(9)
C34 0.081(13) 0.068(11) 0.099(14) 0.014(9) 0.008(10) -0.004(9)
C35 0.081(13) 0.068(11) 0.099(14) 0.014(9) 0.008(10) -0.004(9)

_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 B1 1.482(3) . ?
N1 C1 1.353(3) . ?
N1 C5 1.364(3) . ?
N1 C30 1.476(3) . ?
O1 C33 1.206(16) . ?
B1 C9 1.634(4) . ?
B1 C21 1.650(4) . ?
B1 C12 1.680(4) . ?
C1 C2 1.367(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
N2 C32 1.143(7) . ?
C3 C4 1.378(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.479(4) . ?
C6 C11 1.391(4) . ?
C6 C7 1.396(4) . ?
C7 C8 1.382(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.407(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.404(4) . ?
C10 C11 1.386(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C19 1.422(4) . ?
C12 C13 1.427(4) . ?
C13 C15 1.397(4) . ?
C13 C14 1.520(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9300 . ?
C16 C18 1.379(4) . ?
C16 C17 1.517(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.397(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.516(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C28 1.418(4) . ?
C21 C22 1.427(4) . ?
C22 C24 1.394(4) . ?
C22 C23 1.518(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.382(4) . ?
C24 H24A 0.9300 . ?
C25 C27 1.387(4) . ?
C25 C26 1.520(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.393(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.514(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.415(11) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 H35A 0.7453 . ?
C31 H35B 1.0190 . ?
C31 H35C 1.1358 . ?
C32 H35A 1.5715 . ?
C33 C35 1.48(2) . ?
C33 C34 1.486(17) . ?
C34 C34 1.73(3) 3_755 ?
C34 H34A 0.9600 . ?
C34 H34B 0.9601 . ?
C34 H34C 0.9599 . ?
C35 H35A 0.9599 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
C1 N1 C5 121.1(2) . . ?
C1 N1 C30 118.2(2) . . ?
C5 N1 C30 120.6(2) . . ?
F1 B1 C9 105.2(2) . . ?
F1 B1 C21 110.1(2) . . ?
C9 B1 C21 108.2(2) . . ?
F1 B1 C12 100.6(2) . . ?
C9 B1 C12 115.7(2) . . ?
C21 B1 C12 116.1(2) . . ?
N1 C1 C2 121.8(3) . . ?
N1 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
N1 C5 C4 117.8(3) . . ?
N1 C5 C6 118.5(2) . . ?
C4 C5 C6 123.6(2) . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 C5 122.2(2) . . ?
C7 C6 C5 118.9(2) . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C9 123.1(3) . . ?
C7 C8 H8A 118.4 . . ?
C9 C8 H8A 118.4 . . ?
C10 C9 C8 115.0(3) . . ?
C10 C9 B1 121.3(2) . . ?
C8 C9 B1 123.7(2) . . ?
C11 C10 C9 122.7(3) . . ?
C11 C10 H10A 118.6 . . ?
C9 C10 H10A 118.6 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
C19 C12 C13 115.4(2) . . ?
C19 C12 B1 127.1(2) . . ?
C13 C12 B1 117.2(2) . . ?
C15 C13 C12 121.5(3) . . ?
C15 C13 C14 116.4(3) . . ?
C12 C13 C14 122.1(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 122.3(3) . . ?
C16 C15 H15A 118.8 . . ?
C13 C15 H15A 118.8 . . ?
C18 C16 C15 116.6(3) . . ?
C18 C16 C17 121.1(3) . . ?
C15 C16 C17 122.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 123.5(3) . . ?
C16 C18 H18A 118.3 . . ?
C19 C18 H18A 118.3 . . ?
C18 C19 C12 120.6(3) . . ?
C18 C19 C20 115.6(2) . . ?
C12 C19 C20 123.7(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C28 C21 C22 115.6(2) . . ?
C28 C21 B1 123.2(2) . . ?
C22 C21 B1 121.0(2) . . ?
C24 C22 C21 120.9(3) . . ?
C24 C22 C23 116.7(2) . . ?
C21 C22 C23 122.3(2) . . ?
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 . . ?
C25 C24 C22 122.8(3) . . ?
C25 C24 H24A 118.6 . . ?
C22 C24 H24A 118.6 . . ?
C24 C25 C27 116.7(3) . . ?
C24 C25 C26 121.7(3) . . ?
C27 C25 C26 121.6(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 C28 122.6(3) . . ?
C25 C27 H27A 118.7 . . ?
C28 C27 H27A 118.7 . . ?
C27 C28 C21 121.3(3) . . ?
C27 C28 C29 116.4(2) . . ?
C21 C28 C29 122.4(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N1 C30 H30A 109.5 . . ?
N1 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N1 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C31 H35A 87.6 . . ?
H31A C31 H35A 56.8 . . ?
H31B C31 H35A 68.9 . . ?
H31C C31 H35A 161.7 . . ?
C32 C31 H35B 107.5 . . ?
H31A C31 H35B 68.0 . . ?
H31B C31 H35B 141.1 . . ?
H31C C31 H35B 45.2 . . ?
H35A C31 H35B 124.7 . . ?
C32 C31 H35C 137.1 . . ?
H31A C31 H35C 113.1 . . ?
H31B C31 H35C 50.6 . . ?
H31C C31 H35C 60.6 . . ?
H35A C31 H35C 111.2 . . ?
H35B C31 H35C 93.2 . . ?
N2 C32 C31 176.7(8) . . ?
N2 C32 H35A 148.8 . . ?
C31 C32 H35A 28.3 . . ?
O1 C33 C35 131(3) . . ?
O1 C33 C34 125(3) . . ?
C35 C33 C34 103(3) . . ?
C33 C34 C34 169(3) . 3_755 ?
C33 C34 H34A 109.5 . . ?
C34 C34 H34A 62.5 3_755 . ?
C33 C34 H34B 109.5 . . ?
C34 C34 H34B 68.2 3_755 . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.4 . . ?
C34 C34 H34C 81.6 3_755 . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 110.9 . . ?
C33 C35 H35B 109.1 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 108.4 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.080

# Attachment '4F-sorted.cif'

data_xl
_database_code_depnum_ccdc_archive 'CCDC 738718'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 B F N S'
_chemical_formula_weight         443.41

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   22.51(3)
_cell_length_b                   22.51(3)
_cell_length_c                   17.90(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9071(22)
_cell_formula_units_Z            16
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1948
_cell_measurement_theta_min      4.599
_cell_measurement_theta_max      39.963

_exptl_crystal_description       yellow
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3776
_exptl_absorpt_coefficient_mu    0.168
_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      110(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            22185
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         24.00
_reflns_number_total             3557
_reflns_number_gt                2426
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEX
_computing_cell_refinement       APEX
_computing_data_reduction        APEX
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0415P)^2^+21.0000P] 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         3557
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
S1 S 0.37871(3) 0.91756(4) 0.03447(5) 0.0259(2) Uani 1 1 d . . .
F1 F 0.29332(7) 0.85778(8) -0.04677(10) 0.0278(5) Uani 1 1 d . . .
N1 N 0.50942(11) 1.00340(11) 0.13827(15) 0.0250(6) Uani 1 1 d . . .
B1 B 0.34738(16) 0.82745(16) -0.0708(2) 0.0250(9) Uani 1 1 d . . .
C1 C 0.51489(15) 1.05131(14) 0.18336(19) 0.0310(8) Uani 1 1 d . . .
H1A H 0.5508 1.0579 0.2077 0.037 Uiso 1 1 calc R . .
C2 C 0.46997(15) 1.08971(15) 0.19398(19) 0.0322(9) Uani 1 1 d . . .
H2A H 0.4748 1.1227 0.2247 0.039 Uiso 1 1 calc R . .
C3 C 0.41690(15) 1.07940(15) 0.15858(19) 0.0318(8) Uani 1 1 d . . .
H3A H 0.3851 1.1052 0.1652 0.038 Uiso 1 1 calc R . .
C4 C 0.41143(15) 1.03087(14) 0.11362(19) 0.0286(8) Uani 1 1 d . . .
H4A H 0.3753 1.0240 0.0900 0.034 Uiso 1 1 calc R . .
C5 C 0.45772(14) 0.99146(13) 0.10185(18) 0.0240(8) Uani 1 1 d . . .
C6 C 0.45033(14) 0.94097(13) 0.05323(18) 0.0247(8) Uani 1 1 d . . .
C7 C 0.48835(14) 0.90688(14) 0.01136(18) 0.0254(8) Uani 1 1 d . . .
H7A H 0.5294 0.9115 0.0126 0.030 Uiso 1 1 calc R . .
C8 C 0.46033(14) 0.86492(14) -0.03292(18) 0.0244(8) Uani 1 1 d . . .
H8A H 0.4813 0.8396 -0.0644 0.029 Uiso 1 1 calc R . .
C9 C 0.39984(14) 0.86332(13) -0.02714(18) 0.0239(8) Uani 1 1 d . . .
C10 C 0.36088(13) 0.84027(14) -0.15989(18) 0.0241(8) Uani 1 1 d . . .
C11 C 0.33950(14) 0.89097(14) -0.19713(19) 0.0267(8) Uani 1 1 d . . .
C12 C 0.30382(15) 0.93837(15) -0.1588(2) 0.0341(9) Uani 1 1 d . . .
H12A H 0.2937 0.9688 -0.1941 0.051 Uiso 1 1 calc R . .
H12B H 0.3268 0.9553 -0.1190 0.051 Uiso 1 1 calc R . .
H12C H 0.2681 0.9213 -0.1388 0.051 Uiso 1 1 calc R . .
C13 C 0.35085(14) 0.90002(15) -0.27254(19) 0.0309(8) Uani 1 1 d . . .
H13A H 0.3354 0.9337 -0.2955 0.037 Uiso 1 1 calc R . .
C14 C 0.38384(15) 0.86142(16) -0.3144(2) 0.0336(9) Uani 1 1 d . . .
C15 C 0.39347(18) 0.87054(18) -0.3969(2) 0.0461(10) Uani 1 1 d . . .
H15A H 0.4177 0.8389 -0.4162 0.069 Uiso 1 1 calc R . .
H15B H 0.4131 0.9079 -0.4050 0.069 Uiso 1 1 calc R . .
H15C H 0.3558 0.8706 -0.4221 0.069 Uiso 1 1 calc R . .
C16 C 0.40694(15) 0.81314(15) -0.2782(2) 0.0334(9) Uani 1 1 d . . .
H16A H 0.4310 0.7870 -0.3047 0.040 Uiso 1 1 calc R . .
C17 C 0.39585(14) 0.80170(14) -0.20310(19) 0.0287(8) Uani 1 1 d . . .
C18 C 0.42169(16) 0.74494(15) -0.1725(2) 0.0364(9) Uani 1 1 d . . .
H18A H 0.4439 0.7252 -0.2109 0.055 Uiso 1 1 calc R . .
H18B H 0.3901 0.7195 -0.1557 0.055 Uiso 1 1 calc R . .
H18C H 0.4474 0.7540 -0.1313 0.055 Uiso 1 1 calc R . .
C19 C 0.33397(14) 0.75743(14) -0.05195(18) 0.0253(8) Uani 1 1 d . . .
C20 C 0.28589(14) 0.73074(15) -0.0895(2) 0.0300(8) Uani 1 1 d . . .
C21 C 0.24744(17) 0.76456(18) -0.1435(2) 0.0493(11) Uani 1 1 d . . .
H21A H 0.2173 0.7387 -0.1630 0.074 Uiso 1 1 calc R . .
H21B H 0.2714 0.7793 -0.1837 0.074 Uiso 1 1 calc R . .
H21C H 0.2290 0.7973 -0.1181 0.074 Uiso 1 1 calc R . .
C22 C 0.27097(15) 0.67227(15) -0.0780(2) 0.0345(9) Uani 1 1 d . . .
H22A H 0.2398 0.6561 -0.1054 0.041 Uiso 1 1 calc R . .
C23 C 0.30025(15) 0.63661(15) -0.0274(2) 0.0317(9) Uani 1 1 d . . .
C24 C 0.27958(16) 0.57410(15) -0.0130(2) 0.0447(10) Uani 1 1 d . . .
H24A H 0.3048 0.5559 0.0236 0.067 Uiso 1 1 calc R . .
H24B H 0.2812 0.5517 -0.0586 0.067 Uiso 1 1 calc R . .
H24C H 0.2395 0.5748 0.0051 0.067 Uiso 1 1 calc R . .
C25 C 0.34689(14) 0.66202(14) 0.00970(19) 0.0277(8) Uani 1 1 d . . .
H25A H 0.3679 0.6391 0.0438 0.033 Uiso 1 1 calc R . .
C26 C 0.36419(14) 0.72053(14) -0.00129(18) 0.0253(8) Uani 1 1 d . . .
C27 C 0.41706(15) 0.74032(15) 0.04311(19) 0.0328(9) Uani 1 1 d . . .
H27A H 0.4306 0.7082 0.0739 0.049 Uiso 1 1 calc R . .
H27B H 0.4061 0.7733 0.0741 0.049 Uiso 1 1 calc R . .
H27C H 0.4483 0.7521 0.0097 0.049 Uiso 1 1 calc R . .
C28 C 0.56214(14) 0.96648(15) 0.1301(2) 0.0307(8) Uani 1 1 d . . .
H28A H 0.5937 0.9823 0.1602 0.046 Uiso 1 1 calc R . .
H28B H 0.5742 0.9660 0.0786 0.046 Uiso 1 1 calc R . .
H28C H 0.5533 0.9267 0.1460 0.046 Uiso 1 1 calc R . .

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
S1 0.0211(4) 0.0256(5) 0.0309(5) -0.0014(4) -0.0012(4) -0.0009(4)
F1 0.0225(10) 0.0286(10) 0.0324(11) 0.0012(9) -0.0003(8) 0.0015(8)
N1 0.0246(15) 0.0245(15) 0.0260(16) 0.0060(13) -0.0016(13) -0.0026(12)
B1 0.021(2) 0.027(2) 0.026(2) 0.0019(17) -0.0008(17) 0.0010(16)
C1 0.036(2) 0.0288(19) 0.029(2) 0.0029(16) -0.0023(17) -0.0107(16)
C2 0.038(2) 0.0287(19) 0.030(2) -0.0025(16) 0.0048(17) -0.0075(17)
C3 0.032(2) 0.0270(19) 0.037(2) -0.0010(17) 0.0063(17) 0.0011(15)
C4 0.0277(19) 0.0240(18) 0.034(2) -0.0001(16) 0.0008(16) -0.0022(15)
C5 0.0258(18) 0.0212(17) 0.0249(19) 0.0081(15) 0.0000(15) -0.0044(14)
C6 0.0232(17) 0.0220(17) 0.029(2) 0.0030(15) -0.0036(15) -0.0008(14)
C7 0.0218(17) 0.0266(18) 0.028(2) 0.0032(15) 0.0024(15) -0.0003(14)
C8 0.0260(18) 0.0233(17) 0.0239(19) 0.0004(15) 0.0029(15) 0.0012(14)
C9 0.0306(19) 0.0207(17) 0.0204(18) 0.0029(14) -0.0011(15) 0.0016(14)
C10 0.0198(17) 0.0250(18) 0.0276(19) 0.0024(15) -0.0045(15) -0.0052(14)
C11 0.0213(17) 0.0312(19) 0.027(2) 0.0015(16) -0.0039(15) -0.0059(14)
C12 0.035(2) 0.031(2) 0.036(2) 0.0053(17) -0.0011(17) 0.0029(16)
C13 0.0293(19) 0.032(2) 0.032(2) 0.0087(17) -0.0056(17) -0.0059(16)
C14 0.032(2) 0.038(2) 0.030(2) 0.0022(18) -0.0023(17) -0.0145(17)
C15 0.052(3) 0.055(3) 0.031(2) -0.003(2) 0.0035(19) -0.017(2)
C16 0.0296(19) 0.035(2) 0.035(2) -0.0119(18) 0.0055(17) -0.0099(16)
C17 0.0259(18) 0.0271(19) 0.033(2) -0.0011(16) -0.0010(16) -0.0039(15)
C18 0.039(2) 0.034(2) 0.037(2) -0.0042(17) 0.0087(18) 0.0037(17)
C19 0.0225(17) 0.0283(18) 0.0251(19) -0.0018(15) 0.0040(15) -0.0017(15)
C20 0.0229(18) 0.033(2) 0.034(2) -0.0049(17) 0.0033(16) -0.0028(15)
C21 0.037(2) 0.051(3) 0.060(3) 0.006(2) -0.025(2) -0.0105(19)
C22 0.0236(18) 0.037(2) 0.043(2) -0.0063(18) 0.0035(17) -0.0073(16)
C23 0.0286(19) 0.0266(19) 0.040(2) -0.0031(17) 0.0125(17) -0.0021(15)
C24 0.039(2) 0.030(2) 0.065(3) -0.004(2) 0.016(2) -0.0020(17)
C25 0.0257(18) 0.0262(18) 0.031(2) 0.0035(16) 0.0071(16) 0.0048(15)
C26 0.0239(18) 0.0254(18) 0.027(2) -0.0016(16) 0.0030(15) -0.0004(14)
C27 0.034(2) 0.031(2) 0.033(2) 0.0026(17) -0.0059(17) 0.0031(16)
C28 0.0235(18) 0.036(2) 0.033(2) 0.0012(16) -0.0077(16) 0.0024(15)

_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
S1 C9 1.713(4) . ?
S1 C6 1.729(4) . ?
F1 B1 1.460(4) . ?
N1 C1 1.353(4) . ?
N1 C5 1.361(4) . ?
N1 C28 1.456(4) . ?
B1 C9 1.630(5) . ?
B1 C19 1.640(5) . ?
B1 C10 1.649(6) . ?
C1 C2 1.344(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.441(5) . ?
C6 C7 1.372(5) . ?
C7 C8 1.385(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.366(5) . ?
C8 H8A 0.9300 . ?
C10 C17 1.404(5) . ?
C10 C11 1.407(5) . ?
C11 C13 1.389(5) . ?
C11 C12 1.501(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.367(5) . ?
C13 H13A 0.9300 . ?
C14 C16 1.368(5) . ?
C14 C15 1.507(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.391(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.507(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.409(5) . ?
C19 C26 1.405(5) . ?
C20 C22 1.374(5) . ?
C20 C21 1.504(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.378(5) . ?
C22 H22A 0.9300 . ?
C23 C25 1.368(5) . ?
C23 C24 1.504(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.387(5) . ?
C25 H25A 0.9300 . ?
C26 C27 1.499(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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 S1 C6 94.79(16) . . ?
C1 N1 C5 121.4(3) . . ?
C1 N1 C28 116.2(3) . . ?
C5 N1 C28 122.4(3) . . ?
C2 C1 N1 121.9(3) . . ?
C2 C1 H1A 119.0 . . ?
N1 C1 H1A 119.0 . . ?
F1 B1 C9 103.4(3) . . ?
F1 B1 C19 103.6(3) . . ?
C9 B1 C19 120.7(3) . . ?
F1 B1 C10 110.9(3) . . ?
C9 B1 C10 104.1(3) . . ?
C19 B1 C10 113.6(3) . . ?
C1 C2 C3 118.7(3) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 122.4(3) . . ?
C3 C4 H4A 118.8 . . ?
C5 C4 H4A 118.8 . . ?
N1 C5 C4 116.4(3) . . ?
N1 C5 C6 122.9(3) . . ?
C4 C5 C6 120.7(3) . . ?
C7 C6 C5 134.3(3) . . ?
C7 C6 S1 107.8(2) . . ?
C5 C6 S1 117.7(2) . . ?
C6 C7 C8 114.2(3) . . ?
C6 C7 H7A 122.9 . . ?
C8 C7 H7A 122.9 . . ?
C9 C8 C7 115.4(3) . . ?
C9 C8 H8A 122.3 . . ?
C7 C8 H8A 122.3 . . ?
C8 C9 B1 134.3(3) . . ?
C8 C9 S1 107.9(2) . . ?
B1 C9 S1 117.4(2) . . ?
C17 C10 C11 115.6(3) . . ?
C17 C10 B1 121.9(3) . . ?
C11 C10 B1 122.5(3) . . ?
C13 C11 C10 121.1(3) . . ?
C13 C11 C12 116.0(3) . . ?
C10 C11 C12 122.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 122.7(3) . . ?
C14 C13 H13A 118.7 . . ?
C11 C13 H13A 118.7 . . ?
C16 C14 C13 116.8(3) . . ?
C16 C14 C15 121.2(3) . . ?
C13 C14 C15 121.9(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 122.5(3) . . ?
C14 C16 H16A 118.8 . . ?
C17 C16 H16A 118.8 . . ?
C16 C17 C10 121.2(3) . . ?
C16 C17 C18 116.1(3) . . ?
C10 C17 C18 122.7(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C26 115.3(3) . . ?
C20 C19 B1 117.0(3) . . ?
C26 C19 B1 127.7(3) . . ?
C22 C20 C19 121.6(3) . . ?
C22 C20 C21 116.2(3) . . ?
C19 C20 C21 122.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 122.7(3) . . ?
C20 C22 H22A 118.7 . . ?
C23 C22 H22A 118.7 . . ?
C25 C23 C22 116.3(3) . . ?
C25 C23 C24 123.1(3) . . ?
C22 C23 C24 120.6(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 122.9(3) . . ?
C23 C25 H25A 118.5 . . ?
C26 C25 H25A 118.5 . . ?
C25 C26 C19 121.1(3) . . ?
C25 C26 C27 115.5(3) . . ?
C19 C26 C27 123.4(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.055