Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002

data_global
_database_code_CSD                  186794

_journal_coden_Cambridge      182


loop_
_publ_author_name
'Dhandapani Venkataraman'
'Marianny Y. Combariza'
'Jason E. Field'
'Richard W. Vachet'

_publ_contact_author_name     	'Prof Dhandapani Venkataraman'  
_publ_contact_author_address 
;
Chemistry
University of Massachusetts
710 N. Pleasant Street
701 Lederle Graduate Research Tower
Amherst
01003
UNITED STATES OF AMERICA
;


_publ_contact_author_email 'dv@chem.umass.edu '
_publ_contact_author_fax '413-545-4490 '
_publ_contact_author_phone '413-545-2028 '


_publ_requested_journal       'Chemical Communications'

_publ_section_title
;
Spontaneous Assmebly of a Hydrogen-Bonded Tetrahedron
;

_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(1999). maXus  Computer Program for the Solution and Refinement of
Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan
& The University of Glasgow.

Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.

Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276,
edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326,
New York:Academic Press.

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Sheldrick, G. M. (1997).  SHELXL97.  Program for the Refinement of Crystal
Structures.  University of Gottingen, Germany.
;



_audit_creation_method 'maXus'


_chemical_compound_source        'Local laboratory'
_exptl_crystal_description       'Cube'
_exptl_crystal_colour            'Colourless'
_cell_measurement_temperature     90
_refine_ls_hydrogen_treatment    'noref'


# Submission details
_publ_requested_journal 'Chemical Communications'
_diffrn_measurement_device  'KappaCCD'
_computing_data_collection  'KappaCCD'
_computing_data_reduction  'Denzo and Scalepak (Otwinowski & Minor, 1997)'

_diffrn_radiation_source  'fine-focus sealed tube'
_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    -14
_diffrn_reflns_limit_l_max     14

loop_
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id all


_diffrn_orient_matrix_type 'X=UH'
_diffrn_orient_matrix_UB_11   -0.04270
_diffrn_orient_matrix_UB_12   -0.03200
_diffrn_orient_matrix_UB_13   -0.03361
_diffrn_orient_matrix_UB_21    0.04636
_diffrn_orient_matrix_UB_22   -0.03149
_diffrn_orient_matrix_UB_23   -0.02892
_diffrn_orient_matrix_UB_31   -0.00210
_diffrn_orient_matrix_UB_32   -0.04429
_diffrn_orient_matrix_UB_33    0.04485

_cell_formula_units_Z     8
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method  'not measured'
_exptl_special_details
;
?
;
_chemical_formula_weight    377.352
_diffrn_radiation_type    ' MoK\a'

loop_
_symmetry_equiv_pos_as_xyz
'+X,+Y,+Z'
'-X+ 1/2,+Z+ 1/2,-Y+ 1/2'
'-X+ 1/2,-Z+ 1/2,+Y+ 1/2'
'-Z+ 1/2,-Y+ 1/2,+X+ 1/2'
'+Y,-Z,-X'
'-Z,+X,-Y'
'-Z+ 1/2,+Y+ 1/2,-X+ 1/2'
'-Y+ 1/2,+X+ 1/2,-Z+ 1/2'
'-Z,-X,+Y'
'+X,-Y,-Z'
'+Y+ 1/2,-X+ 1/2,-Z+ 1/2'
'+X+ 1/2,-Z+ 1/2,-Y+ 1/2'
'-X,+Y,-Z'
'-Y,-Z,+X'
'-X,-Y,+Z'
'+Y+ 1/2,+X+ 1/2,+Z+ 1/2'
'-Y,+Z,-X'
'+X+ 1/2,+Z+ 1/2,+Y+ 1/2'
'+Z+ 1/2,+Y+ 1/2,+X+ 1/2'
'+Z,-X,-Y'
'+Z,+X,+Y'
'-Y+ 1/2,-X+ 1/2,+Z+ 1/2'
'+Y,+Z,+X'
'+Z+ 1/2,-Y+ 1/2,-X+ 1/2'

_symmetry_space_group_name_H-M 'P -4 3 n      '
_symmetry_cell_setting 'Cubic'
_chemical_formula_moiety 'C21 H15 N O6 '
_chemical_formula_sum    'C21 H15 N O6 '
_chemical_name_systematic
;
?
;
_cell_length_a           15.8558(3)
_cell_length_b           15.8558(3)
_cell_length_c           15.8558(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume            3986.25(13)
_diffrn_reflns_number   3027
_diffrn_reflns_theta_max  27.41
_diffrn_reflns_theta_min   4.26
_diffrn_reflns_theta_full  27.41
_cell_measurement_reflns_used     1674
_cell_measurement_theta_min        4.076
_cell_measurement_theta_max        27.485
_diffrn_measurement_method       'CCD'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution   'SIR92 (Altomare et al., 1994)'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_exptl_absorpt_correction_type  none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

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'

_exptl_absorpt_coefficient_mu     0.105
_reflns_number_total              1518
_reflns_number_gt                 1327
_reflns_threshold_expression      >2sigma(I)

_computing_structure_refinement   '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^)+(0.1432P)^2^+1.9066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.011(5)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    1(3)
_refine_ls_number_reflns          1518
_refine_ls_number_parameters      91
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0843
_refine_ls_R_factor_gt            0.0752
_refine_ls_wR_factor_ref          0.2255
_refine_ls_wR_factor_gt           0.2101
_refine_ls_goodness_of_fit_ref    1.086
_refine_ls_restrained_S_all       1.086
_refine_ls_shift/su_max           0.004
_refine_ls_shift/su_mean          0.001

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
O1 O 0.33910(19) 0.07967(17) 0.02799(18) 0.0605(8) Uani 1 1 d . . .
O2 O 0.2182(3) 0.0818(3) 0.0955(3) 0.0995(14) Uani 1 1 d . . .
N1 N 0.2160 0.2160 0.2160 0.0391(9) Uani 1 3 d S . .
C1 C 0.26198(17) 0.25710(18) 0.15042(17) 0.0381(7) Uani 1 1 d . . .
C2 C 0.2968(2) 0.2106(2) 0.08212(18) 0.0420(7) Uani 1 1 d . . .
C3 C 0.3433(2) 0.2530(2) 0.02149(18) 0.0464(8) Uani 1 1 d . . .
C4 C 0.3550(2) 0.3402(2) 0.0257(2) 0.0501(8) Uani 1 1 d . . .
C5 C 0.3204(2) 0.3848(2) 0.0919(2) 0.0501(9) Uani 1 1 d . . .
C6 C 0.2753(2) 0.3437(2) 0.1545(2) 0.0449(7) Uani 1 1 d . . .
C7 C 0.2827(2) 0.1182(2) 0.0696(2) 0.0476(8) Uani 1 1 d . . .
C8 C 0.0986(10) -0.0986(10) 0.0986(10) 0.183(8) Uiso 1 3 d S . .
C9 C 0.0594(14) -0.0526(14) 0.1552(13) 0.172(6) Uiso 0.67 1 d P . .
H3 H 0.3671 0.2229 -0.0228 0.056 Uiso 1 1 calc R . .
H4 H 0.3858 0.3679 -0.0157 0.060 Uiso 1 1 calc R . .
H5 H 0.3274 0.4429 0.0945 0.060 Uiso 1 1 calc R . .
H6 H 0.2538 0.3743 0.1996 0.054 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
O1 0.0620(15) 0.0486(13) 0.0708(17) -0.0098(12) 0.0019(13) -0.0015(12)
O2 0.099(3) 0.092(2) 0.107(3) -0.052(2) 0.042(2) -0.050(2)
N1 0.0391(9) 0.0391(9) 0.0391(9) 0.0025(10) 0.0025(10) 0.0025(10)
C1 0.0355(13) 0.0439(15) 0.0347(14) 0.0027(11) -0.0012(11) 0.0039(11)
C2 0.0395(14) 0.0529(17) 0.0336(14) 0.0012(12) -0.0053(11) 0.0007(12)
C3 0.0440(16) 0.062(2) 0.0329(14) 0.0025(13) -0.0038(12) 0.0065(13)
C4 0.0411(15) 0.065(2) 0.0438(16) 0.0171(15) 0.0027(13) 0.0039(14)
C5 0.0452(17) 0.0458(17) 0.059(2) 0.0130(15) 0.0026(14) 0.0072(13)
C6 0.0438(15) 0.0428(15) 0.0479(17) 0.0045(12) 0.0050(13) 0.0073(12)
C7 0.0439(17) 0.0575(19) 0.0413(15) -0.0155(13) -0.0034(13) 0.0000(14)

_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 C7 1.268(4) . ?
O2 C7 1.245(5) . ?
N1 C1 1.427(3) 23 ?
N1 C1 1.427(3) . ?
N1 C1 1.427(3) 21 ?
C1 C6 1.390(4) . ?
C1 C2 1.422(4) . ?
C2 C3 1.385(5) . ?
C2 C7 1.495(5) . ?
C3 C4 1.397(5) . ?
C4 C5 1.379(5) . ?
C5 C6 1.386(5) . ?
C8 C9 1.31(2) 20 ?
C8 C9 1.31(2) . ?
C8 C9 1.31(2) 14 ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

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 N1 C1 118.13(5) 23 . ?
C1 N1 C1 118.13(5) 23 21 ?
C1 N1 C1 118.13(5) . 21 ?
C6 C1 C2 119.2(3) . . ?
C6 C1 N1 119.6(2) . . ?
C2 C1 N1 121.1(2) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 C7 117.6(3) . . ?
C1 C2 C7 123.5(3) . . ?
C2 C3 C4 121.2(3) . . ?
C5 C4 C3 119.4(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C1 120.6(3) . . ?
O2 C7 O1 121.9(3) . . ?
O2 C7 C2 122.2(3) . . ?
O1 C7 C2 115.9(3) . . ?
C9 C8 C9 116.1(10) 20 . ?
C9 C8 C9 116.1(10) 20 14 ?
C9 C8 C9 116.1(10) . 14 ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?

_diffrn_measured_fraction_theta_max    0.992
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.436
_refine_diff_density_min   -0.407
_refine_diff_density_rms    0.070