# 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

_audit_creation_method           SHELXL-97
_publ_contact_author_name        'Piero Sozzani'
_publ_contact_author_address     
;
Dept.Materials Science
University of Milano Bicocca
Via R. Cozzi 53
I-20125 Milan
ITALY
;
_publ_contact_author_email       piero.sozzani@mater.unimib.it
_publ_section_title              
;
A single crystal imprints macroscopic orientation to xenon atoms
;
loop_
_publ_author_name
'P. Sozzani'
'S. Bracco'
'A. Comotti'
'L. Ferretti'
'M. Mauri'
'R. Simonutti'



data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 625332'

_chemical_name_common            tris-o-phenylenedioxyspirocyclotriphosphazene

_chemical_formula_sum            'C18 H12 N3 O6 P3'
_chemical_formula_weight         459.23
_chemical_melting_point          249

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 63/m'
_symmetry_Int_Tables_number      176

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

_cell_length_a                   11.454(5)
_cell_length_b                   11.454(5)
_cell_length_c                   10.160(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1154.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    266
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      28.14

_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.293

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_number            8016
_diffrn_reflns_av_R_equivalents  0.1693
_diffrn_reflns_av_sigmaI/netI    0.1257
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         28.14
_reflns_number_total             949
_reflns_number_gt                862
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlis
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0001P)^2^+25.1800P] 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_number_reflns         949
_refine_ls_number_parameters     49
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1920
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.3027
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_restrained_S_all      1.447
_refine_ls_shift/su_max          0.107
_refine_ls_shift/su_mean         0.032

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 0.5430(4) 0.1836(5) 0.7500 0.0249(11) Uani 1 2 d S . .
O1 O 0.4611(9) 0.0830(9) 0.6313(8) 0.037(2) Uani 1 1 d . . .
N1 N 0.6895(17) 0.2101(17) 0.7500 0.041(4) Uani 1 2 d S . .
C1 C 0.3526(14) -0.0335(13) 0.6821(12) 0.037(3) Uani 1 1 d . . .
C2 C 0.2572(15) -0.1399(15) 0.6091(15) 0.052(4) Uani 1 1 d . . .
H2 H 0.2593 -0.1400 0.5176 0.067 Uiso 1 1 calc R . .
C3 C 0.1570(15) -0.2476(17) 0.6809(14) 0.067(6) Uani 1 1 d . . .
H3 H 0.0889 -0.3208 0.6361 0.087 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
P1 0.014(2) 0.023(2) 0.026(2) 0.000 0.000 0.0003(18)
O1 0.044(6) 0.039(5) 0.020(4) 0.002(4) 0.004(4) 0.014(4)
N1 0.039(10) 0.035(9) 0.052(10) 0.000 0.000 0.021(8)
C1 0.054(9) 0.033(7) 0.029(7) 0.005(6) 0.007(7) 0.026(7)
C2 0.048(9) 0.044(9) 0.030(7) -0.005(7) -0.003(7) -0.001(7)
C3 0.040(9) 0.063(11) 0.040(8) -0.005(8) -0.009(7) -0.018(8)

_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 N1 1.548(17) . ?
P1 N1 1.598(17) 3_665 ?
P1 O1 1.606(9) . ?
P1 O1 1.606(9) 10_557 ?
O1 C1 1.391(16) . ?
N1 P1 1.598(17) 2_655 ?
C1 C2 1.377(18) . ?
C1 C1 1.38(2) 10_557 ?
C2 C3 1.398(19) . ?
C3 C3 1.40(3) 10_557 ?

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
N1 P1 N1 118.2(11) . 3_665 ?
N1 P1 O1 109.2(6) . . ?
N1 P1 O1 110.5(5) 3_665 . ?
N1 P1 O1 109.2(6) . 10_557 ?
N1 P1 O1 110.5(5) 3_665 10_557 ?
O1 P1 O1 97.3(7) . 10_557 ?
C1 O1 P1 109.4(7) . . ?
P1 N1 P1 121.8(11) . 2_655 ?
C2 C1 C1 122.6(8) . 10_557 ?
C2 C1 O1 125.6(11) . . ?
C1 C1 O1 111.8(6) 10_557 . ?
C1 C2 C3 116.0(13) . . ?
C3 C3 C2 121.4(8) 10_557 . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        28.14
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.525
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.128