# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2008

data_global
_journal_coden_Cambridge         440
_publ_section_title              
;
New branched macrocyclic ligand and its side-arm, two urea-based
receptors for anions: synthesis, binding studies and crystal structure
;
_publ_requested_journal          'New Journal of Chemistry'
_publ_contact_author_name        'Vieri Fusi'
_publ_contact_author_address     
;Institute of Chemical Sciences,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;
_publ_contact_author_email       vieri@uniurb.it
_publ_contact_author_phone       +390722378347
_publ_contact_author_fax         +390722350032
loop_
_publ_author_name
_publ_author_address

'Formica, Mauro'
;Institute of Chemical Sciences,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;
'Fusi, Vieri'
;Institute of Chemical Sciences,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;
'Paoli, Paola'
;Department of Energy Engineering "S. Stecco",
University of Florence,
Via S. Marta, 3
I-50139 Florence
Italy
;
'Piersanti, Giovanni'
;Institute of Pharmaceutical Chemistry,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;
'Rossi, Patrizia'
;Department of Energy Engineering "S. Stecco",
University of Florence,
Via S. Marta, 3
I-50139 Florence
Italy
;
'Zappia, Giovanni'
;Institute of Pharmaceutical Chemistry,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;
'Orlando, Pierfrancesco'
;Institute of Pharmaceutical Chemistry,
University of Urbino,
P.za Rinascimento 6,
I-61029 Urbino,
Italy
;

data_L2
_database_code_depnum_ccdc_archive 'CCDC 677798'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 N4 O5'
_chemical_formula_weight         312.33

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.793(2)
_cell_length_b                   11.479(5)
_cell_length_c                   11.615(4)
_cell_angle_alpha                117.05(4)
_cell_angle_beta                 93.32(3)
_cell_angle_gamma                105.24(3)
_cell_volume                     761.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET)
(compiled Jan 20 2006,12:36:28)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur3 4 circles diffractometer'
_diffrn_measurement_method       'intensity from \w scans'
_diffrn_detector_area_resol_mean 16.4547
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7383
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.1268
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         27.19
_reflns_number_total             2767
_reflns_number_gt                1285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET)
(compiled Jan 20 2006,12:36:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET)
(compiled Jan 20 2006,12:36:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET)
(compiled Jan 20 2006,12:36:28)
;
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farruggia, 1997)'
_computing_publication_material  'PARST97 (Nardelli, 1995)'

_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^)+(0.0612P)^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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2767
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_restrained_S_all      0.818
_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
O1W O 0.9260(3) -0.6685(3) 1.0608(2) 0.0482(6) Uani 1 1 d . . .
O1 O 0.7200(2) -0.55917(16) 0.85176(15) 0.0376(5) Uani 1 1 d . . .
O2 O 0.2003(2) -0.81885(17) 0.97986(15) 0.0381(5) Uani 1 1 d . . .
O3 O 0.4946(3) -1.12521(18) 1.38582(17) 0.0451(5) Uani 1 1 d . . .
O4 O 0.1705(3) -1.13958(19) 1.35745(18) 0.0560(6) Uani 1 1 d . . .
N1 N 0.4589(3) -0.5620(2) 0.71991(18) 0.0307(5) Uani 1 1 d . . .
N2 N 0.4897(3) -0.6981(2) 0.9461(2) 0.0333(6) Uani 1 1 d . . .
N3 N 0.5232(3) -0.7888(2) 1.08228(19) 0.0318(6) Uani 1 1 d . . .
N4 N 0.3503(4) -1.0986(2) 1.3451(2) 0.0405(6) Uani 1 1 d . . .
C1 C 0.1742(5) -0.7234(3) 0.5229(3) 0.0418(8) Uani 1 1 d . . .
C2 C 0.2375(4) -0.6040(3) 0.6636(3) 0.0359(7) Uani 1 1 d . . .
C3 C 0.7188(5) -0.5781(4) 0.5748(3) 0.0448(8) Uani 1 1 d . . .
C4 C 0.6102(4) -0.4873(3) 0.6709(3) 0.0369(7) Uani 1 1 d . . .
C5 C 0.5315(4) -0.5924(2) 0.8087(2) 0.0317(6) Uani 1 1 d . . .
C6 C 0.3750(4) -0.6719(3) 0.8575(3) 0.0331(7) Uani 1 1 d . . .
C7 C 0.3917(4) -0.7722(2) 1.0006(2) 0.0301(6) Uani 1 1 d . . .
C8 C 0.4717(4) -0.8645(2) 1.1473(2) 0.0305(6) Uani 1 1 d . . .
C9 C 0.2666(4) -0.9278(3) 1.1501(2) 0.0334(7) Uani 1 1 d . . .
C10 C 0.2303(4) -1.0015(3) 1.2170(2) 0.0342(7) Uani 1 1 d . . .
C11 C 0.3933(4) -1.0154(2) 1.2789(2) 0.0307(6) Uani 1 1 d . . .
C12 C 0.5975(4) -0.9543(3) 1.2780(3) 0.0344(7) Uani 1 1 d . . .
C13 C 0.6342(4) -0.8802(3) 1.2124(2) 0.0327(7) Uani 1 1 d . . .
H1WA H 1.004(4) -0.600(3) 1.096(3) 0.051(11) Uiso 1 1 d . . .
H1WB H 0.994(5) -0.729(3) 1.013(3) 0.080(12) Uiso 1 1 d . . .
H2N H 0.624(4) -0.669(2) 0.961(2) 0.039(8) Uiso 1 1 d . . .
H3N H 0.649(3) -0.7582(19) 1.0826(18) 0.011(6) Uiso 1 1 d . . .
H1A H 0.034(4) -0.743(2) 0.4890(19) 0.031(7) Uiso 1 1 d . . .
H1B H 0.249(4) -0.692(2) 0.466(2) 0.047(8) Uiso 1 1 d . . .
H1C H 0.201(3) -0.807(2) 0.519(2) 0.043(8) Uiso 1 1 d . . .
H2A H 0.212(3) -0.523(2) 0.6674(18) 0.022(6) Uiso 1 1 d . . .
H2B H 0.153(3) -0.628(2) 0.722(2) 0.042(7) Uiso 1 1 d . . .
H3A H 0.623(4) -0.652(3) 0.492(3) 0.065(10) Uiso 1 1 d . . .
H3B H 0.786(4) -0.612(2) 0.617(2) 0.039(7) Uiso 1 1 d . . .
H3C H 0.818(4) -0.521(2) 0.547(2) 0.039(7) Uiso 1 1 d . . .
H4A H 0.533(3) -0.443(2) 0.627(2) 0.034(6) Uiso 1 1 d . . .
H4B H 0.713(3) -0.408(2) 0.748(2) 0.034(7) Uiso 1 1 d . . .
H6A H 0.281(3) -0.761(2) 0.777(2) 0.023(6) Uiso 1 1 d . . .
H6B H 0.293(3) -0.613(2) 0.904(2) 0.038(7) Uiso 1 1 d . . .
H9 H 0.154(3) -0.915(2) 1.1059(19) 0.033(7) Uiso 1 1 d . . .
H10 H 0.092(3) -1.043(2) 1.2189(19) 0.034(7) Uiso 1 1 d . . .
H12 H 0.702(3) -0.966(2) 1.323(2) 0.031(7) Uiso 1 1 d . . .
H13 H 0.775(3) -0.836(2) 1.2056(19) 0.032(6) 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
O1W 0.0239(11) 0.0417(14) 0.0716(16) 0.0240(13) 0.0109(11) 0.0060(12)
O1 0.0211(10) 0.0421(12) 0.0481(11) 0.0248(9) 0.0032(8) 0.0036(8)
O2 0.0186(10) 0.0473(12) 0.0524(11) 0.0291(10) 0.0064(8) 0.0079(8)
O3 0.0484(12) 0.0462(12) 0.0495(12) 0.0286(10) 0.0081(9) 0.0191(10)
O4 0.0384(12) 0.0663(15) 0.0755(14) 0.0492(12) 0.0164(11) 0.0071(10)
N1 0.0249(12) 0.0358(13) 0.0386(13) 0.0231(11) 0.0104(10) 0.0105(10)
N2 0.0216(13) 0.0386(14) 0.0450(14) 0.0266(12) 0.0084(11) 0.0060(11)
N3 0.0178(13) 0.0350(14) 0.0463(14) 0.0250(12) 0.0068(11) 0.0046(11)
N4 0.0430(16) 0.0374(15) 0.0387(14) 0.0179(12) 0.0066(12) 0.0111(12)
C1 0.0285(18) 0.053(2) 0.0438(19) 0.0256(17) 0.0014(14) 0.0102(16)
C2 0.0249(15) 0.0417(19) 0.0486(19) 0.0265(16) 0.0101(13) 0.0134(14)
C3 0.0392(19) 0.059(2) 0.058(2) 0.041(2) 0.0212(18) 0.0214(18)
C4 0.0311(15) 0.0402(18) 0.0450(18) 0.0257(16) 0.0084(14) 0.0107(14)
C5 0.0306(16) 0.0302(16) 0.0315(15) 0.0133(13) 0.0076(13) 0.0090(13)
C6 0.0294(15) 0.0371(18) 0.0379(17) 0.0211(15) 0.0104(14) 0.0124(15)
C7 0.0278(16) 0.0269(16) 0.0347(16) 0.0149(13) 0.0051(13) 0.0079(12)
C8 0.0245(15) 0.0277(15) 0.0376(15) 0.0151(13) 0.0050(12) 0.0079(12)
C9 0.0269(15) 0.0364(17) 0.0411(16) 0.0219(14) 0.0076(13) 0.0110(13)
C10 0.0228(15) 0.0372(17) 0.0438(17) 0.0235(14) 0.0072(13) 0.0044(13)
C11 0.0335(16) 0.0247(15) 0.0329(15) 0.0142(13) 0.0072(13) 0.0076(12)
C12 0.0263(16) 0.0342(17) 0.0431(17) 0.0199(14) 0.0047(13) 0.0092(13)
C13 0.0221(15) 0.0300(16) 0.0470(16) 0.0223(14) 0.0061(13) 0.0035(12)

_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
O1 C5 1.237(3) . ?
O2 C7 1.231(3) . ?
O3 N4 1.230(2) . ?
O4 N4 1.230(3) . ?
N1 C5 1.337(3) . ?
N1 C2 1.462(3) . ?
N1 C4 1.471(3) . ?
N2 C7 1.344(3) . ?
N2 C6 1.438(3) . ?
N3 C7 1.375(3) . ?
N3 C8 1.384(3) . ?
N4 C11 1.462(3) . ?
C1 C2 1.519(4) . ?
C3 C4 1.523(4) . ?
C5 C6 1.522(3) . ?
C8 C13 1.398(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.376(4) . ?
C10 C11 1.369(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.366(3) . ?

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
C5 N1 C2 124.0(2) . . ?
C5 N1 C4 118.3(2) . . ?
C2 N1 C4 117.7(2) . . ?
C7 N2 C6 121.4(2) . . ?
C7 N3 C8 128.2(2) . . ?
O3 N4 O4 122.7(2) . . ?
O3 N4 C11 118.9(2) . . ?
O4 N4 C11 118.5(2) . . ?
N1 C2 C1 112.7(2) . . ?
N1 C4 C3 112.9(2) . . ?
O1 C5 N1 122.7(2) . . ?
O1 C5 C6 119.0(2) . . ?
N1 C5 C6 118.3(2) . . ?
N2 C6 C5 108.0(2) . . ?
O2 C7 N2 122.3(2) . . ?
O2 C7 N3 123.4(2) . . ?
N2 C7 N3 114.3(2) . . ?
N3 C8 C13 117.9(2) . . ?
N3 C8 C9 123.9(2) . . ?
C13 C8 C9 118.2(2) . . ?
C10 C9 C8 119.8(2) . . ?
C11 C10 C9 120.3(2) . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 N4 119.3(2) . . ?
C12 C11 N4 119.4(2) . . ?
C13 C12 C11 118.5(2) . . ?
C12 C13 C8 121.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.816
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.049