# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_contact_author_name        'Thorfinnur Gunnlaugsson'
_publ_contact_author_address     
;
School of Chemistry
Trinity College Dublin
Dublin
Dublin
Dublin 2
REPUBLIC OF IRELAND
;

_publ_section_title              
;
pH driven self-assembly of a ternary lanthanide
luminescence complex: The sensing of anions using a
beta-diketonate-Eu(III) displacement assay
;
_publ_contact_author_email       GUNNLAUT@TCD.IE
loop_
_publ_author_name
T.Gunnlaugsson
'C.M.G.dos Santos'
T.McCabe
S.Plush

# Attachment 'X-ray structure of 1 revised.cif'

data_cs062m
_database_code_depnum_ccdc_archive 'CCDC 616591'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H42 Cl N7 O3'
_chemical_formula_weight         464.06

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'
Cl Cl 0.1484 0.1585 '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/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                   15.1926(14)
_cell_length_b                   11.0971(10)
_cell_length_c                   15.5763(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.215(2)
_cell_angle_gamma                90.00
_cell_volume                     2448.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    396(2)
_cell_measurement_reflns_used    25078
_cell_measurement_theta_min      5.0
_cell_measurement_theta_max      29.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813726
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      396(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  'Bruker Smart Apex'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24370
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.38
_reflns_number_total             6074
_reflns_number_gt                5244
_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^)+(0.0629P)^2^+1.1260P] 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         6074
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.154
_refine_ls_shift/su_mean         0.002

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
Cl1 Cl 0.21658(3) 0.95288(4) 0.05040(3) 0.03930(13) Uani 1 1 d . . .
O3 O 0.89827(8) 0.61586(10) 0.99745(7) 0.0304(2) Uani 1 1 d . . .
O1 O 0.95772(8) 1.11330(10) 0.63502(7) 0.0326(3) Uani 1 1 d . . .
O2 O 1.14775(8) 0.70316(10) 0.74979(9) 0.0334(3) Uani 1 1 d . . .
N5 N 0.75838(8) 0.78929(11) 0.65364(8) 0.0212(2) Uani 1 1 d . . .
H5A H 0.7515 0.7120 0.6349 0.025 Uiso 1 1 calc R . .
H5B H 0.8195 0.8088 0.6679 0.025 Uiso 1 1 calc R . .
N7 N 0.95081(8) 0.76015(10) 0.68332(8) 0.0190(2) Uani 1 1 d . . .
N4 N 0.83770(8) 0.92683(11) 0.54000(8) 0.0217(2) Uani 1 1 d . . .
N6 N 0.89693(8) 0.74546(11) 0.84256(8) 0.0221(2) Uani 1 1 d . . .
N2 N 1.18955(8) 0.89961(12) 0.76565(9) 0.0259(3) Uani 1 1 d . . .
N3 N 0.88357(9) 1.25424(11) 0.52989(8) 0.0264(3) Uani 1 1 d . . .
N1 N 0.96658(9) 0.76562(11) 1.09699(8) 0.0249(3) Uani 1 1 d . . .
C18 C 0.89547(10) 1.14052(13) 0.56200(9) 0.0223(3) Uani 1 1 d . . .
C17 C 0.82630(10) 1.04787(13) 0.50168(9) 0.0239(3) Uani 1 1 d . . .
H17A H 0.7625 1.0749 0.4911 0.029 Uiso 1 1 calc R . .
H17B H 0.8337 1.0447 0.4424 0.029 Uiso 1 1 calc R . .
C13 C 1.02352(9) 0.84702(12) 0.73261(9) 0.0193(3) Uani 1 1 d . . .
H13A H 1.0182 0.8631 0.7918 0.023 Uiso 1 1 calc R . .
H13B H 1.0108 0.9219 0.6982 0.023 Uiso 1 1 calc R . .
C3 C 0.96145(10) 0.65603(13) 0.82913(10) 0.0237(3) Uani 1 1 d . . .
H3A H 0.9492 0.5786 0.8514 0.028 Uiso 1 1 calc R . .
H3B H 1.0258 0.6788 0.8656 0.028 Uiso 1 1 calc R . .
C5 C 0.94175(10) 0.74464(13) 0.58684(9) 0.0226(3) Uani 1 1 d . . .
H5C H 0.8931 0.6852 0.5583 0.027 Uiso 1 1 calc R . .
H5D H 1.0008 0.7134 0.5852 0.027 Uiso 1 1 calc R . .
C1 C 0.73602(10) 0.79797(14) 0.73841(10) 0.0264(3) Uani 1 1 d . . .
H1A H 0.6700 0.7789 0.7243 0.032 Uiso 1 1 calc R . .
H1B H 0.7471 0.8796 0.7622 0.032 Uiso 1 1 calc R . .
C7 C 0.74695(10) 0.86223(14) 0.50350(10) 0.0258(3) Uani 1 1 d . . .
H7A H 0.7574 0.7793 0.4899 0.031 Uiso 1 1 calc R . .
H7B H 0.7061 0.9001 0.4470 0.031 Uiso 1 1 calc R . .
C6 C 0.91706(10) 0.86126(13) 0.53031(10) 0.0238(3) Uani 1 1 d . . .
H6A H 0.9720 0.9134 0.5493 0.029 Uiso 1 1 calc R . .
H6B H 0.9020 0.8417 0.4659 0.029 Uiso 1 1 calc R . .
C8 C 0.70088(10) 0.86579(14) 0.57510(10) 0.0256(3) Uani 1 1 d . . .
H8A H 0.6988 0.9479 0.5956 0.031 Uiso 1 1 calc R . .
H8B H 0.6368 0.8353 0.5492 0.031 Uiso 1 1 calc R . .
C9 C 0.93079(10) 0.80092(13) 0.93284(9) 0.0232(3) Uani 1 1 d . . .
H9A H 0.8918 0.8706 0.9315 0.028 Uiso 1 1 calc R . .
H9B H 0.9947 0.8295 0.9458 0.028 Uiso 1 1 calc R . .
C10 C 0.93090(10) 0.71847(13) 1.01165(10) 0.0220(3) Uani 1 1 d . . .
C2 C 0.79734(10) 0.71095(14) 0.81047(10) 0.0263(3) Uani 1 1 d . . .
H2A H 0.7764 0.7092 0.8624 0.032 Uiso 1 1 calc R . .
H2B H 0.7901 0.6305 0.7845 0.032 Uiso 1 1 calc R . .
C4 C 0.95224(10) 0.64305(12) 0.72879(10) 0.0223(3) Uani 1 1 d . . .
H4A H 1.0047 0.5956 0.7260 0.027 Uiso 1 1 calc R . .
H4B H 0.8945 0.5997 0.6954 0.027 Uiso 1 1 calc R . .
C12 C 1.00381(11) 0.88850(14) 1.11538(11) 0.0288(3) Uani 1 1 d . . .
H12A H 1.0539 0.8982 1.0922 0.043 Uiso 1 1 calc R . .
H12B H 1.0276 0.9030 1.1806 0.043 Uiso 1 1 calc R . .
H12C H 0.9543 0.9449 1.0855 0.043 Uiso 1 1 calc R . .
C14 C 1.12551(10) 0.80968(13) 0.74944(9) 0.0219(3) Uani 1 1 d . . .
C19 C 0.94474(12) 1.35002(14) 0.58265(11) 0.0324(3) Uani 1 1 d . . .
H19A H 0.9127 1.3946 0.6154 0.049 Uiso 1 1 calc R . .
H19B H 0.9604 1.4031 0.5416 0.049 Uiso 1 1 calc R . .
H19C H 1.0015 1.3156 0.6258 0.049 Uiso 1 1 calc R . .
C11 C 0.96122(12) 0.69456(15) 1.17348(10) 0.0307(3) Uani 1 1 d . . .
H11A H 0.9026 0.6511 1.1540 0.046 Uiso 1 1 calc R . .
H11B H 0.9646 0.7471 1.2235 0.046 Uiso 1 1 calc R . .
H11C H 1.0129 0.6386 1.1934 0.046 Uiso 1 1 calc R . .
C20 C 0.80504(12) 1.29477(15) 0.44870(11) 0.0323(3) Uani 1 1 d . . .
H20A H 0.7708 1.2261 0.4158 0.048 Uiso 1 1 calc R . .
H20B H 0.8291 1.3401 0.4094 0.048 Uiso 1 1 calc R . .
H20C H 0.7637 1.3448 0.4675 0.048 Uiso 1 1 calc R . .
C16 C 1.16835(11) 1.02630(15) 0.77368(13) 0.0352(4) Uani 1 1 d . . .
H16A H 1.1087 1.0461 0.7270 0.053 Uiso 1 1 calc R . .
H16B H 1.2170 1.0755 0.7660 0.053 Uiso 1 1 calc R . .
H16C H 1.1654 1.0407 0.8333 0.053 Uiso 1 1 calc R . .
C15 C 1.28971(11) 0.86973(17) 0.80138(13) 0.0385(4) Uani 1 1 d . . .
H15A H 1.3150 0.8826 0.8667 0.058 Uiso 1 1 calc R . .
H15B H 1.3223 0.9201 0.7725 0.058 Uiso 1 1 calc R . .
H15C H 1.2978 0.7868 0.7884 0.058 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
Cl1 0.0356(2) 0.0309(2) 0.0579(3) 0.01932(18) 0.02474(19) 0.01506(16)
O3 0.0392(6) 0.0231(5) 0.0293(5) 0.0007(4) 0.0127(5) -0.0065(5)
O1 0.0354(6) 0.0252(5) 0.0251(5) 0.0025(4) -0.0038(4) -0.0006(4)
O2 0.0249(5) 0.0247(6) 0.0509(7) -0.0011(5) 0.0140(5) 0.0050(4)
N5 0.0183(5) 0.0207(6) 0.0243(6) -0.0016(4) 0.0075(4) -0.0020(4)
N7 0.0196(5) 0.0172(5) 0.0210(5) -0.0024(4) 0.0082(4) -0.0011(4)
N4 0.0185(5) 0.0233(6) 0.0221(6) 0.0004(4) 0.0059(4) -0.0019(4)
N6 0.0220(6) 0.0231(6) 0.0225(6) -0.0001(4) 0.0097(5) 0.0021(5)
N2 0.0167(5) 0.0291(7) 0.0301(6) -0.0043(5) 0.0062(5) -0.0006(5)
N3 0.0280(6) 0.0236(6) 0.0227(6) 0.0026(5) 0.0033(5) 0.0019(5)
N1 0.0276(6) 0.0256(6) 0.0233(6) -0.0007(5) 0.0112(5) -0.0003(5)
C18 0.0227(6) 0.0237(7) 0.0204(6) 0.0006(5) 0.0079(5) 0.0014(5)
C17 0.0224(7) 0.0262(7) 0.0199(6) 0.0026(5) 0.0040(5) -0.0001(5)
C13 0.0189(6) 0.0174(6) 0.0222(6) -0.0029(5) 0.0081(5) 0.0002(5)
C3 0.0265(7) 0.0203(7) 0.0260(7) 0.0020(5) 0.0115(6) 0.0041(5)
C5 0.0239(7) 0.0234(7) 0.0217(6) -0.0047(5) 0.0097(5) -0.0008(5)
C1 0.0222(7) 0.0322(8) 0.0271(7) -0.0018(6) 0.0115(6) 0.0020(6)
C7 0.0216(7) 0.0298(8) 0.0225(7) -0.0003(6) 0.0039(5) -0.0050(6)
C6 0.0231(7) 0.0281(7) 0.0221(6) -0.0021(5) 0.0103(5) -0.0016(5)
C8 0.0177(6) 0.0283(7) 0.0280(7) 0.0029(6) 0.0051(5) 0.0000(5)
C9 0.0288(7) 0.0189(6) 0.0242(7) 0.0003(5) 0.0125(5) 0.0001(5)
C10 0.0211(6) 0.0227(7) 0.0240(7) 0.0010(5) 0.0103(5) 0.0017(5)
C2 0.0255(7) 0.0301(8) 0.0259(7) 0.0013(6) 0.0124(6) -0.0012(6)
C4 0.0243(7) 0.0170(6) 0.0277(7) -0.0012(5) 0.0118(5) 0.0009(5)
C12 0.0286(7) 0.0281(8) 0.0299(7) -0.0063(6) 0.0109(6) -0.0024(6)
C14 0.0204(6) 0.0255(7) 0.0197(6) -0.0014(5) 0.0074(5) 0.0013(5)
C19 0.0413(9) 0.0242(7) 0.0277(7) -0.0005(6) 0.0077(7) -0.0021(7)
C11 0.0335(8) 0.0358(9) 0.0233(7) 0.0030(6) 0.0108(6) -0.0008(7)
C20 0.0339(8) 0.0290(8) 0.0276(7) 0.0068(6) 0.0035(6) 0.0074(6)
C16 0.0226(7) 0.0261(8) 0.0517(10) -0.0071(7) 0.0074(7) -0.0055(6)
C15 0.0175(7) 0.0431(10) 0.0511(10) -0.0064(8) 0.0079(7) 0.0002(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
O3 C10 1.2296(18) . ?
O1 C18 1.2252(17) . ?
O2 C14 1.2288(18) . ?
N5 C1 1.4809(18) . ?
N5 C8 1.4857(18) . ?
N7 C13 1.4579(17) . ?
N7 C5 1.4687(17) . ?
N7 C4 1.4763(18) . ?
N4 C17 1.4545(18) . ?
N4 C6 1.4619(18) . ?
N4 C7 1.4734(18) . ?
N6 C9 1.4482(18) . ?
N6 C3 1.4622(18) . ?
N6 C2 1.4624(19) . ?
N2 C14 1.3522(19) . ?
N2 C15 1.4567(19) . ?
N2 C16 1.458(2) . ?
N3 C18 1.3452(19) . ?
N3 C19 1.455(2) . ?
N3 C20 1.4605(18) . ?
N1 C10 1.3466(19) . ?
N1 C11 1.4554(19) . ?
N1 C12 1.464(2) . ?
C18 C17 1.526(2) . ?
C13 C14 1.5321(18) . ?
C3 C4 1.5248(19) . ?
C5 C6 1.534(2) . ?
C1 C2 1.518(2) . ?
C7 C8 1.517(2) . ?
C9 C10 1.5305(19) . ?

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 N5 C8 116.16(11) . . ?
C13 N7 C5 112.89(11) . . ?
C13 N7 C4 116.91(11) . . ?
C5 N7 C4 111.55(11) . . ?
C17 N4 C6 113.42(11) . . ?
C17 N4 C7 109.58(11) . . ?
C6 N4 C7 114.18(12) . . ?
C9 N6 C3 113.98(11) . . ?
C9 N6 C2 113.78(11) . . ?
C3 N6 C2 115.95(12) . . ?
C14 N2 C15 119.01(13) . . ?
C14 N2 C16 124.15(12) . . ?
C15 N2 C16 114.80(13) . . ?
C18 N3 C19 120.20(12) . . ?
C18 N3 C20 124.65(13) . . ?
C19 N3 C20 114.76(13) . . ?
C10 N1 C11 118.41(13) . . ?
C10 N1 C12 122.95(13) . . ?
C11 N1 C12 118.46(12) . . ?
O1 C18 N3 122.09(13) . . ?
O1 C18 C17 122.25(13) . . ?
N3 C18 C17 115.67(12) . . ?
N4 C17 C18 114.60(11) . . ?
N7 C13 C14 115.97(11) . . ?
N6 C3 C4 113.15(11) . . ?
N7 C5 C6 113.67(11) . . ?
N5 C1 C2 109.91(12) . . ?
N4 C7 C8 108.67(11) . . ?
N4 C6 C5 113.60(11) . . ?
N5 C8 C7 107.48(12) . . ?
N6 C9 C10 114.94(12) . . ?
O3 C10 N1 121.98(13) . . ?
O3 C10 C9 121.73(13) . . ?
N1 C10 C9 116.28(12) . . ?
N6 C2 C1 111.62(12) . . ?
N7 C4 C3 112.87(11) . . ?
O2 C14 N2 122.08(13) . . ?
O2 C14 C13 121.35(13) . . ?
N2 C14 C13 116.56(12) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055