# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Jonathan Steed'
'A Beeby'
'M Paterson'
'Adam N. Swinburne'

_publ_contact_author_name        'Jonathan Steed'
_publ_contact_author_email       JON.STEED@DUR.AC.UK

_publ_section_title              
;
A Quinolinium-Derived Turn-off Fluorescent Anion Sensor
;

# Attachment 'compound_2.CIF'

data_y:\groupc~1\adamsw~1\09srv99\work\9s099m
_database_code_depnum_ccdc_archive 'CCDC 755341'
#TrackingRef 'compound_2.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F6 N P'
_chemical_formula_weight         365.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   9.7798(3)
_cell_length_b                   11.4208(3)
_cell_length_c                   15.9407(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.2150(10)
_cell_angle_gamma                90.00
_cell_volume                     1506.37(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4060
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      29.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_T_max  0.9522
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25074
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4060
_reflns_number_gt                2396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XSEED
_computing_publication_material  XSEED

_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^)+(0.0305P)^2^+1.1459P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4060
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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
P1 P 0.21148(8) 0.95708(5) 0.23664(5) 0.02351(15) Uani 1 1 d . . .
F3 F 0.32525(18) 1.05346(12) 0.23315(11) 0.0352(4) Uani 1 1 d . . .
F5 F 0.29147(18) 0.85797(12) 0.20578(11) 0.0350(4) Uani 1 1 d . . .
F6 F 0.09886(19) 0.85882(14) 0.24225(13) 0.0476(4) Uani 1 1 d . . .
F1 F 0.34392(19) 0.93461(14) 0.35126(10) 0.0417(4) Uani 1 1 d . . .
F4 F 0.07883(19) 0.97968(14) 0.12283(11) 0.0477(5) Uani 1 1 d . . .
N1 N 0.3521(2) 0.50468(16) 0.30675(13) 0.0202(4) Uani 1 1 d . . .
C9 C 0.4561(3) 0.41835(19) 0.36962(16) 0.0185(5) Uani 1 1 d . . .
C4 C 0.6123(3) 0.45310(19) 0.44710(16) 0.0189(4) Uani 1 1 d . . .
C7 C 0.5154(3) 0.2197(2) 0.42598(17) 0.0242(5) Uani 1 1 d . . .
H7 H 0.4835 0.1400 0.4195 0.029 Uiso 1 1 calc R . .
C8 C 0.4099(3) 0.2999(2) 0.35868(17) 0.0218(5) Uani 1 1 d . . .
H8 H 0.3067 0.2759 0.3053 0.026 Uiso 1 1 calc R . .
C1 C 0.3971(3) 0.61639(19) 0.31717(17) 0.0223(5) Uani 1 1 d . . .
H1 H 0.3220 0.6729 0.2728 0.027 Uiso 1 1 calc R . .
C5 C 0.7180(3) 0.3670(2) 0.51408(17) 0.0234(5) Uani 1 1 d . . .
H5 H 0.8234 0.3887 0.5663 0.028 Uiso 1 1 calc R . .
C3 C 0.6577(3) 0.5716(2) 0.45623(17) 0.0230(5) Uani 1 1 d . . .
H3 H 0.7627 0.5954 0.5076 0.028 Uiso 1 1 calc R . .
C2 C 0.5503(3) 0.6526(2) 0.39098(17) 0.0246(5) Uani 1 1 d . . .
H2 H 0.5805 0.7326 0.3962 0.029 Uiso 1 1 calc R . .
C11 C 0.1718(3) 0.4203(2) 0.13677(17) 0.0211(5) Uani 1 1 d . . .
C12 C 0.2408(3) 0.4740(2) 0.09001(17) 0.0269(5) Uani 1 1 d . . .
H12 H 0.3058 0.5418 0.1185 0.032 Uiso 1 1 calc R . .
C10 C 0.1836(3) 0.4741(2) 0.22664(16) 0.0222(5) Uani 1 1 d . . .
H10B H 0.1166 0.5458 0.2062 0.027 Uiso 1 1 calc R . .
H10A H 0.1386 0.4185 0.2535 0.027 Uiso 1 1 calc R . .
C6 C 0.6699(3) 0.2526(2) 0.50438(17) 0.0253(5) Uani 1 1 d . . .
H6 H 0.7408 0.1957 0.5506 0.030 Uiso 1 1 calc R . .
C16 C 0.0800(3) 0.3196(2) 0.09521(18) 0.0251(5) Uani 1 1 d . . .
H16 H 0.0357 0.2805 0.1280 0.030 Uiso 1 1 calc R . .
C15 C 0.0524(3) 0.2758(2) 0.00649(18) 0.0278(5) Uani 1 1 d . . .
H15 H -0.0125 0.2080 -0.0222 0.033 Uiso 1 1 calc R . .
C14 C 0.1197(3) 0.3311(2) -0.04021(17) 0.0273(6) Uani 1 1 d . . .
H14 H 0.0999 0.3016 -0.1015 0.033 Uiso 1 1 calc R . .
C13 C 0.2157(3) 0.4292(2) 0.00180(18) 0.0288(6) Uani 1 1 d . . .
H13 H 0.2643 0.4658 -0.0295 0.035 Uiso 1 1 calc R . .
F2 F 0.12949(19) 1.05576(13) 0.26743(12) 0.0431(4) 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
P1 0.0247(3) 0.0227(3) 0.0248(3) -0.0026(3) 0.0143(3) -0.0013(3)
F3 0.0468(9) 0.0308(8) 0.0378(8) -0.0008(7) 0.0290(8) -0.0096(7)
F5 0.0476(9) 0.0262(8) 0.0441(9) 0.0043(7) 0.0330(8) 0.0104(7)
F6 0.0483(10) 0.0382(9) 0.0737(12) -0.0154(8) 0.0442(10) -0.0187(8)
F1 0.0488(10) 0.0466(10) 0.0244(8) 0.0063(7) 0.0160(7) -0.0037(8)
F4 0.0441(10) 0.0419(10) 0.0276(8) -0.0052(7) -0.0007(8) 0.0111(8)
N1 0.0206(10) 0.0214(9) 0.0189(10) -0.0014(8) 0.0109(8) 0.0008(8)
C9 0.0195(11) 0.0213(11) 0.0177(11) -0.0013(9) 0.0119(9) 0.0007(9)
C4 0.0213(11) 0.0205(11) 0.0199(11) -0.0018(9) 0.0144(10) -0.0008(9)
C7 0.0304(13) 0.0191(11) 0.0270(12) -0.0016(10) 0.0179(11) -0.0011(10)
C8 0.0215(12) 0.0226(12) 0.0216(11) -0.0042(9) 0.0117(10) -0.0042(9)
C1 0.0284(13) 0.0178(11) 0.0231(12) 0.0006(9) 0.0153(11) 0.0033(10)
C5 0.0211(12) 0.0277(12) 0.0223(12) -0.0012(10) 0.0120(10) -0.0001(10)
C3 0.0248(12) 0.0229(12) 0.0238(12) -0.0058(10) 0.0147(10) -0.0051(10)
C2 0.0322(13) 0.0177(11) 0.0283(13) -0.0034(10) 0.0192(11) -0.0023(10)
C11 0.0153(11) 0.0213(11) 0.0213(11) 0.0027(9) 0.0062(9) 0.0034(9)
C12 0.0319(13) 0.0191(12) 0.0275(13) 0.0006(10) 0.0143(11) -0.0003(10)
C10 0.0154(11) 0.0259(12) 0.0231(12) 0.0008(9) 0.0088(10) 0.0018(9)
C6 0.0269(13) 0.0248(12) 0.0261(13) 0.0040(10) 0.0154(11) 0.0046(10)
C16 0.0170(11) 0.0275(12) 0.0288(13) 0.0020(10) 0.0110(10) 0.0000(10)
C15 0.0223(12) 0.0254(13) 0.0315(13) -0.0077(11) 0.0116(11) -0.0020(10)
C14 0.0274(13) 0.0281(13) 0.0186(12) -0.0006(10) 0.0070(11) 0.0096(10)
C13 0.0353(14) 0.0263(13) 0.0276(13) 0.0060(10) 0.0187(12) 0.0043(11)
F2 0.0492(10) 0.0356(9) 0.0596(11) -0.0146(8) 0.0391(9) -0.0013(7)

_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
P1 F3 1.5871(15) . ?
P1 F4 1.5910(16) . ?
P1 F5 1.5955(15) . ?
P1 F1 1.5996(16) . ?
P1 F2 1.6043(15) . ?
P1 F6 1.6080(16) . ?
N1 C1 1.331(3) . ?
N1 C9 1.387(3) . ?
N1 C10 1.491(3) . ?
C9 C8 1.407(3) . ?
C9 C4 1.416(3) . ?
C4 C3 1.408(3) . ?
C4 C5 1.414(3) . ?
C7 C8 1.369(3) . ?
C7 C6 1.404(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9500 . ?
C3 C2 1.369(3) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C11 C12 1.387(3) . ?
C11 C16 1.390(3) . ?
C11 C10 1.505(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C6 H6 0.9500 . ?
C16 C15 1.384(3) . ?
C16 H16 0.9500 . ?
C15 C14 1.381(3) . ?
C15 H15 0.9500 . ?
C14 C13 1.384(3) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?

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
F3 P1 F4 90.47(9) . . ?
F3 P1 F5 90.75(8) . . ?
F4 P1 F5 89.96(9) . . ?
F3 P1 F1 89.74(8) . . ?
F4 P1 F1 179.59(10) . . ?
F5 P1 F1 90.39(9) . . ?
F3 P1 F2 89.86(8) . . ?
F4 P1 F2 89.89(9) . . ?
F5 P1 F2 179.37(9) . . ?
F1 P1 F2 89.75(9) . . ?
F3 P1 F6 178.93(10) . . ?
F4 P1 F6 90.59(10) . . ?
F5 P1 F6 89.14(8) . . ?
F1 P1 F6 89.20(9) . . ?
F2 P1 F6 90.25(8) . . ?
C1 N1 C9 121.65(19) . . ?
C1 N1 C10 118.20(18) . . ?
C9 N1 C10 120.13(18) . . ?
N1 C9 C8 122.0(2) . . ?
N1 C9 C4 117.8(2) . . ?
C8 C9 C4 120.2(2) . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 C9 119.6(2) . . ?
C5 C4 C9 118.6(2) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C12 C11 C16 119.0(2) . . ?
C12 C11 C10 121.2(2) . . ?
C16 C11 C10 119.6(2) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
N1 C10 C11 113.60(18) . . ?
N1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
H10B C10 H10A 107.7 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C9 C8 -179.5(2) . . . . ?
C10 N1 C9 C8 2.1(3) . . . . ?
C1 N1 C9 C4 1.1(3) . . . . ?
C10 N1 C9 C4 -177.27(18) . . . . ?
N1 C9 C4 C3 -1.6(3) . . . . ?
C8 C9 C4 C3 179.1(2) . . . . ?
N1 C9 C4 C5 177.73(19) . . . . ?
C8 C9 C4 C5 -1.7(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
N1 C9 C8 C7 -176.9(2) . . . . ?
C4 C9 C8 C7 2.4(3) . . . . ?
C9 N1 C1 C2 0.3(3) . . . . ?
C10 N1 C1 C2 178.7(2) . . . . ?
C3 C4 C5 C6 179.0(2) . . . . ?
C9 C4 C5 C6 -0.3(3) . . . . ?
C5 C4 C3 C2 -178.6(2) . . . . ?
C9 C4 C3 C2 0.7(3) . . . . ?
C4 C3 C2 C1 0.7(3) . . . . ?
N1 C1 C2 C3 -1.2(3) . . . . ?
C16 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C13 -173.8(2) . . . . ?
C1 N1 C10 C11 102.4(2) . . . . ?
C9 N1 C10 C11 -79.2(2) . . . . ?
C12 C11 C10 N1 -51.9(3) . . . . ?
C16 C11 C10 N1 132.9(2) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C10 C11 C16 C15 172.8(2) . . . . ?
C11 C16 C15 C14 1.5(4) . . . . ?
C16 C15 C14 C13 0.7(4) . . . . ?
C15 C14 C13 C12 -1.7(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.068