# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
#TrackingRef 'Cif_complex1a.cif'

_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Shih-Sheng Sun'
_publ_contact_author_email       SSSUN@CHEM.SINICA.EDU.TW

_publ_section_title              
;
Dynamic Self-Assembly of Molecular Capsule via Solvent Polarity
Controlled Reversible Binding of Nitrate Anion with C3
Symmetric tripodal Receptor
;
_publ_section_exptl_refinement   
;
The disordered solvent was treated as a diffuse contribution
using the program SQUEEZE (A. Spek, Platon Library). The
crystal diffracted poorly, which led to a high R factor of 0.1953
for complex 1a.
;
loop_
_publ_author_name
'Ashutosh Sharan Singh'
'Shih Sheng Sun'

data_Complex1a.CIF
_database_code_depnum_ccdc_archive 'CCDC 777052'
#TrackingRef 'Cif_complex1a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H49 N5 O12'
_chemical_formula_sum            'C48 H49 N5 O12'
_chemical_formula_weight         887.92

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           trigonal
_symmetry_space_group_name_H-M   'P -3'
_symmetry_space_group_name_Hall  '-P 3'

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

_cell_length_a                   15.7160(5)
_cell_length_b                   15.7160(5)
_cell_length_c                   11.4490(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2448.96(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8882
_cell_measurement_theta_min      2.037
_cell_measurement_theta_max      25.028

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8764
_exptl_absorpt_correction_T_max  1.1152
_exptl_absorpt_process_details   
;
?
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13438
_diffrn_reflns_av_R_equivalents  0.1221
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2845
_reflns_number_gt                1619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.2000P)^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    fixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2845
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2508
_refine_ls_R_factor_gt           0.1953
_refine_ls_wR_factor_ref         0.5372
_refine_ls_wR_factor_gt          0.5241
_refine_ls_goodness_of_fit_ref   1.837
_refine_ls_restrained_S_all      1.837
_refine_ls_shift/su_max          0.072
_refine_ls_shift/su_mean         0.021

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 0.7736(8) 0.3948(8) 0.7973(9) 0.046(3) Uani 1 1 d . . .
H1A H 0.7836 0.3743 0.8754 0.055 Uiso 1 1 calc R . .
H1B H 0.7920 0.4649 0.8016 0.055 Uiso 1 1 calc R . .
C2 C 0.8390(8) 0.3822(9) 0.7079(10) 0.055(3) Uani 1 1 d . . .
H2A H 0.9094 0.4249 0.7272 0.066 Uiso 1 1 calc R . .
H2B H 0.8240 0.3131 0.7048 0.066 Uiso 1 1 calc R . .
C3 C 0.8551(8) 0.3985(8) 0.4977(9) 0.045(3) Uani 1 1 d . . .
C4 C 0.9271(8) 0.3702(9) 0.4990(10) 0.053(3) Uani 1 1 d . . .
H4 H 0.9481 0.3553 0.5700 0.063 Uiso 1 1 calc R . .
C5 C 0.9658(8) 0.3650(8) 0.3928(9) 0.043(3) Uani 1 1 d . . .
H5 H 1.0180 0.3511 0.3909 0.052 Uiso 1 1 calc R . .
C6 C 0.9303(7) 0.3795(8) 0.2906(9) 0.040(3) Uani 1 1 d . . .
C7 C 0.8584(7) 0.4070(7) 0.2858(9) 0.043(3) Uani 1 1 d . . .
H7 H 0.8365 0.4188 0.2135 0.051 Uiso 1 1 calc R . .
C8 C 0.8198(7) 0.4163(7) 0.3930(9) 0.042(3) Uani 1 1 d . . .
H8 H 0.7705 0.4345 0.3945 0.051 Uiso 1 1 calc R . .
C9 C 0.9754(9) 0.3705(8) 0.1781(11) 0.055(3) Uani 1 1 d . . .
C10 C 0.9485(8) 0.3215(8) -0.0262(8) 0.042(3) Uani 1 1 d . . .
C11 C 1.0417(8) 0.3822(8) -0.0818(10) 0.050(3) Uani 1 1 d . . .
H11 H 1.0876 0.4425 -0.0460 0.060 Uiso 1 1 calc R . .
C12 C 1.0660(8) 0.3565(9) -0.1829(9) 0.051(3) Uani 1 1 d . . .
H12 H 1.1296 0.3972 -0.2149 0.061 Uiso 1 1 calc R . .
C13 C 0.9999(9) 0.2715(9) -0.2417(10) 0.056(3) Uani 1 1 d . . .
C15 C 0.9046(9) 0.2132(9) -0.1937(11) 0.063(4) Uani 1 1 d . . .
H15 H 0.8569 0.1569 -0.2348 0.076 Uiso 1 1 calc R . .
C16 C 0.8809(8) 0.2374(7) -0.0888(10) 0.050(3) Uani 1 1 d . . .
H16 H 0.8172 0.1966 -0.0573 0.060 Uiso 1 1 calc R . .
C17 C 1.1144(12) 0.2883(14) -0.3897(17) 0.116(7) Uani 1 1 d . . .
H17A H 1.1150 0.2579 -0.4642 0.175 Uiso 1 1 calc R . .
H17B H 1.1571 0.2803 -0.3337 0.175 Uiso 1 1 calc R . .
H17C H 1.1384 0.3584 -0.4017 0.175 Uiso 1 1 calc R . .
N1 N 0.6667 0.3333 0.7623(11) 0.035(3) Uani 1 3 d S . .
H1' H 0.6667 0.3333 0.6664 0.042 Uiso 1 3 d SR . .
N2 N 0.9205(6) 0.3451(6) 0.0805(7) 0.041(2) Uani 1 1 d . . .
H2 H 0.8636 0.3431 0.0835 0.050 Uiso 1 1 calc R . .
N3 N 0.6667 0.3333 0.0706(10) 0.027(3) Uani 1 3 d S . .
O1 O 0.8149(5) 0.4117(6) 0.5966(6) 0.053(2) Uani 1 1 d . . .
O2 O 1.0618(6) 0.3856(6) 0.1760(7) 0.059(2) Uani 1 1 d . . .
O3 O 1.0176(7) 0.2425(7) -0.3455(9) 0.084(3) Uani 1 1 d . . .
O4 O 0.7023(5) 0.2781(5) 0.0693(6) 0.046(2) 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 0.051(7) 0.053(7) 0.038(6) 0.009(5) 0.012(5) 0.029(6)
C2 0.036(6) 0.060(7) 0.063(8) 0.009(6) -0.003(6) 0.018(6)
C3 0.048(6) 0.064(7) 0.036(6) 0.005(5) 0.013(5) 0.037(6)
C4 0.042(6) 0.071(8) 0.042(6) 0.011(6) 0.003(5) 0.026(6)
C5 0.039(6) 0.051(7) 0.044(6) 0.005(5) 0.011(5) 0.025(5)
C6 0.042(6) 0.047(6) 0.033(6) -0.008(5) 0.004(5) 0.023(5)
C7 0.036(6) 0.048(6) 0.042(6) 0.004(5) 0.005(5) 0.019(5)
C8 0.041(6) 0.047(6) 0.047(6) -0.006(5) 0.001(5) 0.028(5)
C9 0.043(7) 0.051(7) 0.069(8) 0.006(6) 0.005(6) 0.023(6)
C10 0.041(6) 0.062(7) 0.032(5) -0.006(5) -0.009(5) 0.032(6)
C11 0.034(6) 0.039(6) 0.062(7) 0.004(6) -0.001(6) 0.006(5)
C12 0.047(7) 0.057(7) 0.038(6) 0.005(6) 0.007(5) 0.018(6)
C13 0.069(8) 0.062(8) 0.049(7) -0.013(6) -0.001(6) 0.042(7)
C15 0.048(7) 0.051(7) 0.070(9) -0.023(6) 0.008(6) 0.009(6)
C16 0.037(6) 0.033(6) 0.066(8) 0.021(6) 0.012(6) 0.006(5)
C17 0.081(12) 0.156(18) 0.118(14) 0.041(13) 0.050(11) 0.064(12)
N1 0.039(5) 0.039(5) 0.028(7) 0.000 0.000 0.019(3)
N2 0.039(5) 0.047(5) 0.032(5) -0.012(4) -0.002(4) 0.017(4)
N3 0.032(5) 0.032(5) 0.016(6) 0.000 0.000 0.016(2)
O1 0.045(5) 0.081(6) 0.042(4) -0.004(4) -0.002(4) 0.039(4)
O2 0.040(5) 0.087(6) 0.052(5) -0.002(4) -0.005(4) 0.032(4)
O3 0.071(6) 0.100(7) 0.087(7) -0.023(6) 0.020(5) 0.047(6)
O4 0.042(4) 0.049(4) 0.051(5) -0.004(4) -0.003(3) 0.025(4)

_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 N1 1.515(11) . ?
C1 C2 1.532(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.468(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.362(12) . ?
C3 C4 1.407(15) . ?
C3 C8 1.407(15) . ?
C4 C5 1.381(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(14) . ?
C6 C9 1.511(15) . ?
C7 C8 1.409(14) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 O2 1.256(13) . ?
C9 N2 1.344(14) . ?
C10 C16 1.408(15) . ?
C10 N2 1.410(12) . ?
C10 C11 1.436(15) . ?
C11 C12 1.343(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(16) . ?
C12 H12 0.9500 . ?
C13 O3 1.351(14) . ?
C13 C15 1.418(17) . ?
C15 C16 1.368(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O3 1.413(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 C1 1.515(11) 3_665 ?
N1 C1 1.515(11) 2_655 ?
N1 H1' 1.0984 . ?
N2 H2 0.8800 . ?
N3 O4 1.246(7) . ?
N3 O4 1.246(7) 2_655 ?
N3 O4 1.246(7) 3_665 ?

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 C1 C2 110.1(9) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O1 C2 C1 104.1(8) . . ?
O1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O1 C3 C4 123.1(10) . . ?
O1 C3 C8 114.8(9) . . ?
C4 C3 C8 122.1(9) . . ?
C5 C4 C3 117.2(10) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C6 C5 C4 121.1(10) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 123.1(9) . . ?
C5 C6 C9 117.8(10) . . ?
C7 C6 C9 119.0(9) . . ?
C8 C7 C6 117.1(10) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
C7 C8 C3 119.2(9) . . ?
C7 C8 H8 120.4 . . ?
C3 C8 H8 120.4 . . ?
O2 C9 N2 120.8(11) . . ?
O2 C9 C6 120.8(11) . . ?
N2 C9 C6 118.4(10) . . ?
C16 C10 N2 119.9(10) . . ?
C16 C10 C11 116.0(9) . . ?
N2 C10 C11 123.9(10) . . ?
C12 C11 C10 122.1(10) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 121.2(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
O3 C13 C12 124.7(11) . . ?
O3 C13 C15 116.8(11) . . ?
C12 C13 C15 118.4(10) . . ?
C16 C15 C13 120.4(11) . . ?
C16 C15 H15 119.8 . . ?
C13 C15 H15 119.8 . . ?
C15 C16 C10 121.7(10) . . ?
C15 C16 H16 119.2 . . ?
C10 C16 H16 119.2 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C1 113.3(5) 3_665 . ?
C1 N1 C1 113.3(5) 3_665 2_655 ?
C1 N1 C1 113.3(5) . 2_655 ?
C1 N1 H1' 105.3 3_665 . ?
C1 N1 H1' 105.3 . . ?
C1 N1 H1' 105.3 2_655 . ?
C9 N2 C10 124.1(9) . . ?
C9 N2 H2 117.9 . . ?
C10 N2 H2 118.0 . . ?
O4 N3 O4 119.98(3) . 2_655 ?
O4 N3 O4 119.98(3) . 3_665 ?
O4 N3 O4 119.98(3) 2_655 3_665 ?
C3 O1 C2 117.5(8) . . ?
C13 O3 C17 119.6(12) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.142