# Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2007


data_global
_journal_name_full               'Green Chemistry'

_journal_coden_Cambridge         1048

_publ_contact_author_name        'Colin Raston'
_publ_contact_author_address     
;
Centre for Strategic Nano-Fabrication
University of Western Australia
School of Biomedical, Biomolecular
35 Stirling Hwy
Crawley
Western Australia
6009
AUSTRALIA
;

_publ_contact_author_email       CLRASTON@CHEM.UWA.EDU.AU

_publ_section_title              
;
PEG mediated synthesis of amino-functionalised
2,4,6-triarylpyridines
;
loop_
_publ_author_name
C.Raston
C.Smith
N.M.Smiyh
A.N.Sobolev

data_ns80
_database_code_depnum_ccdc_archive 'CCDC 634027'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N3, 0.5(H2 O)'
_chemical_formula_sum            'C23 H20 N3 O0.5'
_chemical_formula_weight         346.42

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           Monoclinic
_symmetry_space_group_name_H-M   'C 2'

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

_cell_length_a                   25.390(6)
_cell_length_b                   5.557(2)
_cell_length_c                   13.342(1)
_cell_angle_alpha                90.0
_cell_angle_beta                 93.826(14)
_cell_angle_gamma                90.0
_cell_volume                     1878.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1274
_cell_measurement_theta_min      2.7549
_cell_measurement_theta_max      27.3773

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8186
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_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  'Oxford Diffraction Xcalibur-S, Sapphire CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5684
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.1894
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         27.40
_reflns_number_total             2028
_reflns_number_gt                1116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_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^)+(0.1233P)^2^+0.0125P] 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     SHELXL
_refine_ls_extinction_coef       0.0007(19)
_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   2(10)
_refine_ls_number_reflns         2028
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2378
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_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 0.5000 1.343(7) 0.0000 0.150(13) Uiso 0.50 2 d SP . .
O2W O 0.5000 1.015(6) 0.0000 0.113(9) Uiso 0.50 2 d SP . .
C11 C 0.1245(3) 0.4239(12) 0.6113(6) 0.0226(18) Uani 1 1 d . . .
C12 C 0.0812(3) 0.2689(15) 0.6099(5) 0.0267(19) Uani 1 1 d . . .
H12 H 0.0691 0.1912 0.5492 0.032 Uiso 1 1 calc R . .
C13 C 0.0556(3) 0.2284(14) 0.6977(5) 0.0269(19) Uani 1 1 d . . .
C14 C 0.0744(3) 0.3457(15) 0.7844(6) 0.0298(19) Uani 1 1 d . . .
H14 H 0.0572 0.3246 0.8449 0.036 Uiso 1 1 calc R . .
C15 C 0.1185(3) 0.4945(15) 0.7831(5) 0.0267(18) Uani 1 1 d . . .
N16 N 0.1429(2) 0.5354(13) 0.6978(4) 0.0304(18) Uani 1 1 d . . .
C21 C 0.1544(3) 0.4747(15) 0.5243(5) 0.0242(18) Uani 1 1 d . . .
C22 C 0.1565(3) 0.3190(16) 0.4429(6) 0.030(2) Uani 1 1 d . . .
H22 H 0.1360 0.1760 0.4408 0.036 Uiso 1 1 calc R . .
C23 C 0.1880(3) 0.3697(17) 0.3654(5) 0.029(2) Uani 1 1 d . . .
H23 H 0.1898 0.2576 0.3120 0.035 Uiso 1 1 calc R . .
C24 C 0.2172(3) 0.5821(16) 0.3636(5) 0.027(2) Uani 1 1 d . . .
C25 C 0.2134(3) 0.7419(15) 0.4411(5) 0.0267(19) Uani 1 1 d . . .
H25 H 0.2324 0.8890 0.4403 0.032 Uiso 1 1 calc R . .
C26 C 0.1825(3) 0.6947(14) 0.5204(5) 0.0251(19) Uani 1 1 d . . .
H26 H 0.1801 0.8100 0.5725 0.030 Uiso 1 1 calc R . .
N27 N 0.2490(3) 0.6339(15) 0.2867(5) 0.040(2) Uani 1 1 d . . .
H27A H 0.2668 0.7697 0.2873 0.048 Uiso 1 1 calc R . .
H27B H 0.2514 0.5312 0.2370 0.048 Uiso 1 1 calc R . .
C31 C 0.0082(3) 0.0738(15) 0.6956(6) 0.030(2) Uani 1 1 d . . .
C32 C 0.0048(3) -0.1358(15) 0.6393(6) 0.036(2) Uani 1 1 d . . .
H32 H 0.0334 -0.1787 0.6004 0.043 Uiso 1 1 calc R . .
C33 C -0.0388(3) -0.2843(17) 0.6380(6) 0.040(2) Uani 1 1 d . . .
H33 H -0.0403 -0.4279 0.5992 0.048 Uiso 1 1 calc R . .
C34 C -0.0806(4) -0.2187(18) 0.6947(7) 0.048(3) Uani 1 1 d . . .
H34 H -0.1114 -0.3156 0.6925 0.057 Uiso 1 1 calc R . .
C35 C -0.0779(3) -0.0146(17) 0.7543(6) 0.037(2) Uani 1 1 d . . .
H35 H -0.1060 0.0233 0.7952 0.044 Uiso 1 1 calc R . .
C36 C -0.0349(3) 0.1314(18) 0.7543(6) 0.038(2) Uani 1 1 d . . .
H36 H -0.0336 0.2736 0.7939 0.046 Uiso 1 1 calc R . .
C41 C 0.1396(3) 0.6269(15) 0.8735(6) 0.0264(19) Uani 1 1 d . . .
C42 C 0.1390(3) 0.5392(14) 0.9682(6) 0.0277(19) Uani 1 1 d . . .
H42 H 0.1218 0.3905 0.9788 0.033 Uiso 1 1 calc R . .
C43 C 0.1628(3) 0.6604(15) 1.0500(6) 0.033(2) Uani 1 1 d . . .
H43 H 0.1620 0.5943 1.1156 0.040 Uiso 1 1 calc R . .
C44 C 0.1880(3) 0.8795(14) 1.0358(6) 0.030(2) Uani 1 1 d . . .
C45 C 0.1889(3) 0.9735(15) 0.9403(6) 0.033(2) Uani 1 1 d . . .
H45 H 0.2062 1.1222 0.9298 0.039 Uiso 1 1 calc R . .
C46 C 0.1646(3) 0.8496(14) 0.8595(6) 0.0241(18) Uani 1 1 d . . .
H46 H 0.1647 0.9159 0.7939 0.029 Uiso 1 1 calc R . .
N47 N 0.2125(3) 1.0010(13) 1.1162(5) 0.0386(19) Uani 1 1 d . . .
H47A H 0.2287 1.1382 1.1064 0.046 Uiso 1 1 calc R . .
H47B H 0.2120 0.9413 1.1772 0.046 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
C11 0.026(4) 0.010(4) 0.032(4) 0.002(3) 0.006(3) -0.006(3)
C12 0.020(4) 0.036(5) 0.023(4) -0.005(4) -0.007(3) 0.008(4)
C13 0.019(4) 0.032(5) 0.028(4) 0.002(4) -0.003(3) 0.007(4)
C14 0.023(4) 0.032(5) 0.034(4) 0.004(4) 0.002(3) -0.013(4)
C15 0.025(4) 0.025(4) 0.030(4) 0.004(4) -0.004(3) 0.001(4)
N16 0.016(3) 0.053(5) 0.021(3) 0.003(3) -0.004(3) 0.004(3)
C21 0.013(4) 0.030(4) 0.029(4) 0.001(4) -0.009(3) 0.000(4)
C22 0.020(4) 0.035(5) 0.035(5) -0.010(4) -0.001(3) 0.004(4)
C23 0.014(4) 0.055(6) 0.019(4) -0.014(4) -0.002(3) 0.002(4)
C24 0.011(4) 0.057(6) 0.012(4) 0.007(4) -0.004(3) -0.002(4)
C25 0.021(4) 0.031(5) 0.027(4) 0.006(4) -0.006(3) 0.000(4)
C26 0.015(4) 0.032(5) 0.029(4) -0.009(4) 0.006(3) 0.009(4)
N27 0.029(4) 0.059(5) 0.033(4) 0.000(4) 0.002(3) -0.009(4)
C31 0.017(4) 0.032(5) 0.042(5) 0.015(4) -0.007(3) -0.003(4)
C32 0.032(5) 0.040(5) 0.036(5) -0.008(4) 0.001(4) -0.013(5)
C33 0.033(5) 0.040(5) 0.046(5) 0.010(5) -0.017(4) -0.006(5)
C34 0.028(5) 0.060(7) 0.053(6) 0.027(6) -0.019(4) -0.014(5)
C35 0.021(4) 0.051(6) 0.037(5) 0.018(5) -0.006(4) 0.004(5)
C36 0.022(4) 0.055(6) 0.038(5) 0.007(5) -0.002(4) -0.009(5)
C41 0.016(4) 0.031(5) 0.032(4) -0.002(4) 0.006(3) 0.009(4)
C42 0.020(4) 0.026(5) 0.037(5) 0.004(4) 0.003(3) 0.000(4)
C43 0.038(5) 0.033(5) 0.029(4) 0.002(4) 0.005(4) 0.003(4)
C44 0.036(5) 0.027(5) 0.028(4) -0.014(4) 0.008(4) -0.001(4)
C45 0.029(5) 0.022(5) 0.050(5) 0.011(4) 0.015(4) -0.006(4)
C46 0.020(4) 0.029(4) 0.024(4) 0.000(4) 0.004(3) 0.008(4)
N47 0.051(5) 0.038(4) 0.027(4) 0.001(4) 0.006(3) -0.015(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
C11 N16 1.365(9) . ?
C11 C12 1.397(10) . ?
C11 C21 1.456(10) . ?
C12 C13 1.395(11) . ?
C13 C14 1.385(10) . ?
C13 C31 1.477(11) . ?
C14 C15 1.394(10) . ?
C15 N16 1.350(9) . ?
C15 C41 1.482(11) . ?
C21 C22 1.392(10) . ?
C21 C26 1.418(11) . ?
C22 C23 1.378(11) . ?
C23 C24 1.396(12) . ?
C24 C25 1.371(11) . ?
C24 N27 1.376(9) . ?
C25 C26 1.384(10) . ?
C31 C32 1.386(11) . ?
C31 C36 1.424(11) . ?
C32 C33 1.380(12) . ?
C33 C34 1.393(13) . ?
C34 C35 1.384(13) . ?
C35 C36 1.361(11) . ?
C41 C42 1.355(10) . ?
C41 C46 1.408(11) . ?
C42 C43 1.387(11) . ?
C43 C44 1.394(11) . ?
C44 C45 1.379(11) . ?
C44 N47 1.380(9) . ?
C45 C46 1.389(11) . ?

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
N16 C11 C12 121.0(7) . . ?
N16 C11 C21 114.9(6) . . ?
C12 C11 C21 124.1(7) . . ?
C13 C12 C11 119.9(7) . . ?
C14 C13 C12 118.2(7) . . ?
C14 C13 C31 121.6(7) . . ?
C12 C13 C31 120.2(7) . . ?
C13 C14 C15 120.1(7) . . ?
N16 C15 C14 121.6(7) . . ?
N16 C15 C41 116.2(7) . . ?
C14 C15 C41 122.1(7) . . ?
C15 N16 C11 119.2(7) . . ?
C22 C21 C26 117.5(7) . . ?
C22 C21 C11 123.4(7) . . ?
C26 C21 C11 119.1(7) . . ?
C23 C22 C21 120.8(8) . . ?
C22 C23 C24 121.5(8) . . ?
C25 C24 N27 120.1(8) . . ?
C25 C24 C23 118.0(7) . . ?
N27 C24 C23 121.9(8) . . ?
C24 C25 C26 121.8(8) . . ?
C25 C26 C21 120.2(7) . . ?
C32 C31 C36 117.7(8) . . ?
C32 C31 C13 121.3(7) . . ?
C36 C31 C13 120.9(8) . . ?
C33 C32 C31 122.0(8) . . ?
C32 C33 C34 118.4(9) . . ?
C35 C34 C33 121.1(9) . . ?
C36 C35 C34 119.8(9) . . ?
C35 C36 C31 120.8(9) . . ?
C42 C41 C46 118.2(7) . . ?
C42 C41 C15 123.7(8) . . ?
C46 C41 C15 118.0(7) . . ?
C41 C42 C43 121.9(8) . . ?
C42 C43 C44 119.8(8) . . ?
C45 C44 N47 119.9(8) . . ?
C45 C44 C43 119.5(7) . . ?
N47 C44 C43 120.6(7) . . ?
C44 C45 C46 119.7(8) . . ?
C45 C46 C41 120.9(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N16 C11 C12 C13 0.8(11) . . . . ?
C21 C11 C12 C13 178.9(7) . . . . ?
C11 C12 C13 C14 0.1(11) . . . . ?
C11 C12 C13 C31 177.1(7) . . . . ?
C12 C13 C14 C15 -1.6(11) . . . . ?
C31 C13 C14 C15 -178.6(7) . . . . ?
C13 C14 C15 N16 2.4(12) . . . . ?
C13 C14 C15 C41 178.9(8) . . . . ?
C14 C15 N16 C11 -1.5(11) . . . . ?
C41 C15 N16 C11 -178.3(7) . . . . ?
C12 C11 N16 C15 -0.1(11) . . . . ?
C21 C11 N16 C15 -178.4(7) . . . . ?
N16 C11 C21 C22 154.2(7) . . . . ?
C12 C11 C21 C22 -24.0(11) . . . . ?
N16 C11 C21 C26 -26.6(10) . . . . ?
C12 C11 C21 C26 155.1(7) . . . . ?
C26 C21 C22 C23 4.8(10) . . . . ?
C11 C21 C22 C23 -176.0(7) . . . . ?
C21 C22 C23 C24 -2.5(11) . . . . ?
C22 C23 C24 C25 -0.7(10) . . . . ?
C22 C23 C24 N27 179.7(7) . . . . ?
N27 C24 C25 C26 -179.1(7) . . . . ?
C23 C24 C25 C26 1.4(10) . . . . ?
C24 C25 C26 C21 1.1(11) . . . . ?
C22 C21 C26 C25 -4.1(10) . . . . ?
C11 C21 C26 C25 176.7(7) . . . . ?
C14 C13 C31 C32 -143.1(8) . . . . ?
C12 C13 C31 C32 40.0(11) . . . . ?
C14 C13 C31 C36 34.8(11) . . . . ?
C12 C13 C31 C36 -142.1(8) . . . . ?
C36 C31 C32 C33 0.9(11) . . . . ?
C13 C31 C32 C33 178.9(7) . . . . ?
C31 C32 C33 C34 0.5(12) . . . . ?
C32 C33 C34 C35 -2.5(12) . . . . ?
C33 C34 C35 C36 3.1(12) . . . . ?
C34 C35 C36 C31 -1.7(12) . . . . ?
C32 C31 C36 C35 -0.3(11) . . . . ?
C13 C31 C36 C35 -178.3(7) . . . . ?
N16 C15 C41 C42 -148.3(7) . . . . ?
C14 C15 C41 C42 34.9(11) . . . . ?
N16 C15 C41 C46 27.5(10) . . . . ?
C14 C15 C41 C46 -149.2(7) . . . . ?
C46 C41 C42 C43 -1.0(11) . . . . ?
C15 C41 C42 C43 174.8(7) . . . . ?
C41 C42 C43 C44 0.4(12) . . . . ?
C42 C43 C44 C45 0.0(12) . . . . ?
C42 C43 C44 N47 -179.1(7) . . . . ?
N47 C44 C45 C46 179.5(7) . . . . ?
C43 C44 C45 C46 0.4(12) . . . . ?
C44 C45 C46 C41 -1.1(11) . . . . ?
C42 C41 C46 C45 1.3(11) . . . . ?
C15 C41 C46 C45 -174.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.858
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.858
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.080