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

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Jong Seung Kim'
'Sankarprasad Bhuniya'
'Hyun Jung Kim.'
'Kyoung Chul Ko.'
'Jin Yong Lee.'
'Hongguang Liu.'
'Rakesh Kumar Mahajan'
'Rajiv Puri'

_publ_contact_author_name        'Jong Seung Kim'
_publ_contact_author_email       JONGSKIM@KOREA.AC.KR

_publ_section_title              
;
Fluorescence Turn-On Sensors for HSO4?
;

# Attachment 'JSKim_418.cif'

data_yk982sadp21n
_database_code_depnum_ccdc_archive 'CCDC 746885'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 F3 N O3'
_chemical_formula_weight         333.26

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   9.855(2)
_cell_length_b                   5.4280(11)
_cell_length_c                   26.716(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1428.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    725
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      20.29

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   '(SADABS; Brujer, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            7321
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2796
_reflns_number_gt                1235
_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^)+(0.0716P)^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     SHELXL
_refine_ls_extinction_coef       0.0079(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.001
_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 0.2662(3) 0.5352(6) 0.86809(13) 0.0517(9) Uani 1 1 d . . .
C2 C 0.1860(3) 0.3243(6) 0.87361(11) 0.0455(8) Uani 1 1 d . . .
C3 C 0.0958(3) 0.2623(6) 0.83477(12) 0.0552(9) Uani 1 1 d . . .
H3 H 0.0427 0.1216 0.8377 0.066 Uiso 1 1 calc R . .
C4 C 0.0833(4) 0.4031(7) 0.79235(13) 0.0615(10) Uani 1 1 d . . .
H4 H 0.0222 0.3593 0.7670 0.074 Uiso 1 1 calc R . .
C5 C 0.1629(4) 0.6110(7) 0.78787(13) 0.0615(10) Uani 1 1 d . . .
H5 H 0.1552 0.7072 0.7592 0.074 Uiso 1 1 calc R . .
C6 C 0.2532(4) 0.6779(6) 0.82513(13) 0.0605(10) Uani 1 1 d . . .
H6 H 0.3058 0.8188 0.8216 0.073 Uiso 1 1 calc R . .
C7 C 0.1955(3) 0.1722(6) 0.91751(13) 0.0499(8) Uani 1 1 d . . .
H7 H 0.1420 0.0314 0.9191 0.060 Uiso 1 1 calc R . .
C8 C 0.2791(3) 0.0728(6) 0.99793(11) 0.0461(8) Uani 1 1 d . . .
C9 C 0.1948(3) -0.1264(6) 1.00582(12) 0.0485(8) Uani 1 1 d . . .
H9 H 0.1320 -0.1751 0.9814 0.058 Uiso 1 1 calc R . .
C10 C 0.2057(3) -0.2512(5) 1.05045(12) 0.0454(8) Uani 1 1 d . . .
C11 C 0.1197(3) -0.5930(7) 1.09727(12) 0.0505(9) Uani 1 1 d . . .
C12 C 0.2084(3) -0.5187(6) 1.13794(12) 0.0516(9) Uani 1 1 d . . .
H12 H 0.2071 -0.6077 1.1677 0.062 Uiso 1 1 calc R . .
C13 C 0.2927(3) -0.3258(6) 1.13455(12) 0.0461(8) Uani 1 1 d . . .
C14 C 0.2982(3) -0.1864(5) 1.08870(11) 0.0433(8) Uani 1 1 d . . .
C15 C 0.3836(3) 0.0146(6) 1.07914(12) 0.0500(9) Uani 1 1 d . . .
H15 H 0.4476 0.0632 1.1032 0.060 Uiso 1 1 calc R . .
C16 C 0.3736(3) 0.1392(6) 1.03491(12) 0.0522(9) Uani 1 1 d . . .
H16 H 0.4312 0.2716 1.0293 0.063 Uiso 1 1 calc R . .
C17 C 0.3748(4) -0.2479(7) 1.17930(13) 0.0574(9) Uani 1 1 d . . .
F1 F 0.3364(2) -0.0300(4) 1.19583(8) 0.0942(8) Uani 1 1 d . . .
F2 F 0.5052(2) -0.2255(4) 1.17083(8) 0.0846(8) Uani 1 1 d . . .
F3 F 0.3641(3) -0.4007(5) 1.21747(8) 0.1040(9) Uani 1 1 d . . .
N1 N 0.2749(3) 0.2233(5) 0.95456(10) 0.0511(7) Uani 1 1 d . . .
O1 O 0.3547(3) 0.6062(5) 0.90416(9) 0.0726(8) Uani 1 1 d . . .
H1 H 0.3494 0.5128 0.9282 0.109 Uiso 1 1 calc R . .
O2 O 0.1185(2) -0.4477(4) 1.05540(8) 0.0528(6) Uani 1 1 d . . .
O3 O 0.0466(2) -0.7702(4) 1.09727(8) 0.0636(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.054(2) 0.043(2) 0.058(2) -0.0053(17) -0.0011(17) -0.0022(17)
C2 0.0465(19) 0.0362(19) 0.054(2) 0.0019(16) 0.0003(16) 0.0039(16)
C3 0.050(2) 0.050(2) 0.065(2) -0.0002(19) -0.0102(18) -0.0031(17)
C4 0.063(2) 0.057(2) 0.064(2) 0.0015(19) -0.0110(18) 0.0036(19)
C5 0.073(2) 0.052(2) 0.060(2) 0.0122(19) 0.000(2) 0.002(2)
C6 0.074(2) 0.042(2) 0.065(2) 0.0073(18) -0.002(2) -0.0064(18)
C7 0.0498(19) 0.037(2) 0.062(2) 0.0039(17) -0.0033(17) -0.0057(16)
C8 0.0478(19) 0.042(2) 0.049(2) -0.0011(16) -0.0007(16) -0.0020(16)
C9 0.051(2) 0.041(2) 0.053(2) -0.0016(17) -0.0088(16) -0.0068(16)
C10 0.0417(19) 0.0380(19) 0.056(2) -0.0029(17) 0.0000(16) -0.0060(16)
C11 0.047(2) 0.043(2) 0.061(2) -0.0028(18) -0.0003(17) 0.0011(17)
C12 0.053(2) 0.047(2) 0.055(2) 0.0058(16) -0.0005(17) 0.0035(17)
C13 0.0408(18) 0.044(2) 0.053(2) -0.0066(16) -0.0070(15) 0.0046(16)
C14 0.0412(18) 0.040(2) 0.049(2) -0.0053(15) -0.0095(15) 0.0022(15)
C15 0.047(2) 0.047(2) 0.056(2) -0.0030(17) -0.0077(16) -0.0037(16)
C16 0.0473(19) 0.046(2) 0.063(2) -0.0038(18) -0.0058(17) -0.0092(16)
C17 0.060(3) 0.055(2) 0.057(2) 0.003(2) -0.0113(18) 0.0049(19)
F1 0.1166(19) 0.0850(18) 0.0798(17) -0.0339(13) -0.0283(13) 0.0263(15)
F2 0.0536(14) 0.116(2) 0.0837(15) -0.0063(13) -0.0196(11) -0.0005(12)
F3 0.132(2) 0.109(2) 0.0694(15) 0.0314(15) -0.0386(14) -0.0404(16)
N1 0.0541(17) 0.0487(18) 0.0502(17) 0.0024(14) -0.0065(14) -0.0080(13)
O1 0.0871(18) 0.0614(18) 0.0688(18) 0.0050(13) -0.0150(15) -0.0315(14)
O2 0.0518(14) 0.0474(14) 0.0589(15) 0.0056(12) -0.0099(11) -0.0118(11)
O3 0.0604(15) 0.0497(15) 0.0806(18) 0.0001(13) -0.0008(12) -0.0169(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 1.345(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.400(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.436(4) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.281(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(4) . ?
C8 C16 1.393(4) . ?
C8 N1 1.418(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 O2 1.378(3) . ?
C10 C14 1.402(4) . ?
C11 O3 1.202(3) . ?
C11 O2 1.368(4) . ?
C11 C12 1.440(4) . ?
C12 C13 1.341(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.442(4) . ?
C13 C17 1.493(4) . ?
C14 C15 1.405(4) . ?
C15 C16 1.363(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 F2 1.315(4) . ?
C17 F1 1.320(4) . ?
C17 F3 1.320(4) . ?
O1 H1 0.8200 . ?

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 C6 118.8(3) . . ?
O1 C1 C2 121.3(3) . . ?
C6 C1 C2 120.0(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C7 120.0(3) . . ?
C1 C2 C7 121.8(3) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C2 122.5(3) . . ?
N1 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
C9 C8 C16 119.3(3) . . ?
C9 C8 N1 124.6(3) . . ?
C16 C8 N1 116.1(3) . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 O2 115.2(3) . . ?
C9 C10 C14 123.3(3) . . ?
O2 C10 C14 121.5(3) . . ?
O3 C11 O2 117.7(3) . . ?
O3 C11 C12 125.4(3) . . ?
O2 C11 C12 116.9(3) . . ?
C13 C12 C11 122.4(3) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 C17 119.7(3) . . ?
C14 C13 C17 120.3(3) . . ?
C10 C14 C15 116.5(3) . . ?
C10 C14 C13 117.0(3) . . ?
C15 C14 C13 126.4(3) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C8 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C8 C16 H16 119.2 . . ?
F2 C17 F1 105.2(3) . . ?
F2 C17 F3 106.4(3) . . ?
F1 C17 F3 106.1(3) . . ?
F2 C17 C13 114.0(3) . . ?
F1 C17 C13 111.6(3) . . ?
F3 C17 C13 113.0(3) . . ?
C7 N1 C8 121.0(3) . . ?
C1 O1 H1 109.5 . . ?
C11 O2 C10 121.9(2) . . ?

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
O1 C1 C2 C3 179.7(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
O1 C1 C2 C7 -0.8(5) . . . . ?
C6 C1 C2 C7 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C7 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
O1 C1 C6 C5 -179.5(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C3 C2 C7 N1 -178.7(3) . . . . ?
C1 C2 C7 N1 1.8(5) . . . . ?
C16 C8 C9 C10 1.0(5) . . . . ?
N1 C8 C9 C10 -177.4(3) . . . . ?
C8 C9 C10 O2 -179.9(3) . . . . ?
C8 C9 C10 C14 0.1(5) . . . . ?
O3 C11 C12 C13 176.5(3) . . . . ?
O2 C11 C12 C13 -4.1(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C12 C13 C17 175.7(3) . . . . ?
C9 C10 C14 C15 -1.0(5) . . . . ?
O2 C10 C14 C15 179.0(3) . . . . ?
C9 C10 C14 C13 176.6(3) . . . . ?
O2 C10 C14 C13 -3.4(4) . . . . ?
C12 C13 C14 C10 4.5(4) . . . . ?
C17 C13 C14 C10 -172.0(3) . . . . ?
C12 C13 C14 C15 -178.1(3) . . . . ?
C17 C13 C14 C15 5.4(5) . . . . ?
C10 C14 C15 C16 0.9(4) . . . . ?
C13 C14 C15 C16 -176.5(3) . . . . ?
C14 C15 C16 C8 0.1(5) . . . . ?
C9 C8 C16 C15 -1.1(5) . . . . ?
N1 C8 C16 C15 177.4(3) . . . . ?
C12 C13 C17 F2 128.3(3) . . . . ?
C14 C13 C17 F2 -55.2(4) . . . . ?
C12 C13 C17 F1 -112.8(4) . . . . ?
C14 C13 C17 F1 63.7(4) . . . . ?
C12 C13 C17 F3 6.6(5) . . . . ?
C14 C13 C17 F3 -176.8(3) . . . . ?
C2 C7 N1 C8 178.3(3) . . . . ?
C9 C8 N1 C7 -4.5(5) . . . . ?
C16 C8 N1 C7 177.1(3) . . . . ?
O3 C11 O2 C10 -175.3(3) . . . . ?
C12 C11 O2 C10 5.3(4) . . . . ?
C9 C10 O2 C11 178.4(3) . . . . ?
C14 C10 O2 C11 -1.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 F1 0.93 2.72 3.409(4) 131.3 1_545
C4 H4 F1 0.93 2.77 3.580(4) 145.6 4_565
C5 H5 F2 0.93 2.76 3.522(4) 139.4 4_565
C12 H12 F3 0.93 2.31 2.677(4) 102.7 .
C15 H15 F2 0.93 2.45 3.005(4) 118.3 .
C15 H15 F1 0.93 2.77 3.169(4) 106.9 .
O1 H1 N1 0.82 1.88 2.606(3) 147.4 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050