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

data_global

_journal_coden_Cambridge      182

loop_
_publ_author_name 
'G. Laval'
'W. Clegg'
'C.G. Crane'
'A. Hammershoi'
'A.M. Sargeson' 
'B.T. Golding'

_publ_requested_journal       'Chemical Communications'

_publ_contact_author_name     	'Prof Bernard T Golding'  
_publ_contact_author_address 
;
Chemistry
Newcastle University
Bedson Building
Newcastle upon Tyne
Tyne & Wear
NE1 7RU
UNITED KINGDOM
;

_publ_contact_author_email       'B.T.GOLDING@NCL.AC.UK'

_publ_section_title		
;
Assembly of polyamines via amino acids from three components using
cobalt(III) template methodology
;


data_btg49
_database_code_CSD                  168722

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C11 H28 Cl2 Co N5 O3'
_chemical_formula_weight          408.21

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'
'Cl'  'Cl'   0.1484   0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Co'  'Co'   0.3494   0.9721
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    Pbca

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

_cell_length_a                    8.3623(4)
_cell_length_b                    13.7158(7)
_cell_length_c                    30.2033(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3464.2(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     14612
_cell_measurement_theta_min       2.70
_cell_measurement_theta_max       28.30

_exptl_crystal_description        plate
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.58
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.565
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1712
_exptl_absorpt_coefficient_mu     1.318
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.515
_exptl_absorpt_correction_T_max   0.925
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0
_diffrn_reflns_number             27701
_diffrn_reflns_av_R_equivalents   0.0597
_diffrn_reflns_av_sigmaI/netI     0.0431
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -39
_diffrn_reflns_limit_l_max        40
_diffrn_reflns_theta_min          2.70
_diffrn_reflns_theta_max          28.44
_reflns_number_total              4172
_reflns_number_gt                 3141
_reflns_threshold_expression      I>2\s(I)

_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement   'Bruker SHELXTL'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL and local programs'

_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^)+(0.0351P)^2^+4.0701P] 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     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.00050(12)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          4172
_refine_ls_number_parameters      207
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0631
_refine_ls_R_factor_gt            0.0392
_refine_ls_wR_factor_ref          0.0903
_refine_ls_wR_factor_gt           0.0822
_refine_ls_goodness_of_fit_ref    1.086
_refine_ls_restrained_S_all       1.086
_refine_ls_shift/su_max           0.001
_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
Co Co 0.52030(4) 0.78030(2) 0.113063(11) 0.01003(10) Uani 1 1 d . . .
N1 N 0.3907(3) 0.70803(15) 0.06843(7) 0.0144(5) Uani 1 1 d . . .
H1A H 0.3361 0.7523 0.0513 0.017 Uiso 1 1 calc R . .
H1B H 0.4587 0.6740 0.0501 0.017 Uiso 1 1 calc R . .
N2 N 0.5301(2) 0.66150(15) 0.14964(7) 0.0125(4) Uani 1 1 d . . .
N3 N 0.6234(2) 0.85441(16) 0.15965(7) 0.0126(4) Uani 1 1 d . . .
H3A H 0.7237 0.8299 0.1655 0.015 Uiso 1 1 calc R . .
H3B H 0.6329 0.9189 0.1517 0.015 Uiso 1 1 calc R . .
N4 N 0.4948(3) 0.90037(16) 0.07727(7) 0.0165(5) Uani 1 1 d . . .
H4A H 0.4247 0.8852 0.0548 0.020 Uiso 1 1 calc R . .
H4B H 0.4434 0.9449 0.0951 0.020 Uiso 1 1 calc R . .
N5 N 0.7248(2) 0.74275(16) 0.08640(7) 0.0134(4) Uani 1 1 d . . .
H5A H 0.7800 0.7069 0.1071 0.016 Uiso 1 1 calc R . .
H5B H 0.7026 0.7015 0.0632 0.016 Uiso 1 1 calc R . .
O1 O 0.3267(2) 0.82145(13) 0.14111(6) 0.0146(4) Uani 1 1 d . . .
O2 O 0.2361(2) 0.87474(14) 0.20623(6) 0.0212(4) Uani 1 1 d . . .
C1 C 0.2738(3) 0.6386(2) 0.08814(9) 0.0181(6) Uani 1 1 d . . .
H1C H 0.1963 0.6183 0.0651 0.022 Uiso 1 1 calc R . .
H1D H 0.2136 0.6719 0.1120 0.022 Uiso 1 1 calc R . .
C2 C 0.3561(3) 0.5485(2) 0.10711(9) 0.0209(6) Uani 1 1 d . . .
H2A H 0.2913 0.5226 0.1319 0.025 Uiso 1 1 calc R . .
H2B H 0.3615 0.4975 0.0840 0.025 Uiso 1 1 calc R . .
C3 C 0.5246(3) 0.57018(19) 0.12370(9) 0.0161(5) Uani 1 1 d . . .
H3C H 0.5619 0.5154 0.1424 0.019 Uiso 1 1 calc R . .
H3D H 0.5980 0.5757 0.0981 0.019 Uiso 1 1 calc R . .
C4 C 0.5387(3) 0.65627(19) 0.19198(8) 0.0144(5) Uani 1 1 d . . .
C5 C 0.5458(4) 0.5621(2) 0.21759(9) 0.0252(7) Uani 1 1 d . . .
H5C H 0.4589 0.5191 0.2079 0.038 Uiso 1 1 calc R . .
H5D H 0.5342 0.5758 0.2493 0.038 Uiso 1 1 calc R . .
H5E H 0.6488 0.5301 0.2122 0.038 Uiso 1 1 calc R . .
C6 C 0.5464(3) 0.7455(2) 0.22071(8) 0.0164(6) Uani 1 1 d . . .
H6A H 0.6533 0.7473 0.2348 0.020 Uiso 1 1 calc R . .
H6B H 0.4667 0.7378 0.2447 0.020 Uiso 1 1 calc R . .
C7 C 0.5177(3) 0.84363(19) 0.19865(9) 0.0148(5) Uani 1 1 d . . .
H7 H 0.5383 0.8975 0.2202 0.018 Uiso 1 1 calc R . .
C8 C 0.3458(3) 0.84908(18) 0.18187(9) 0.0143(5) Uani 1 1 d . . .
C9 C 0.6303(4) 0.9527(2) 0.05644(10) 0.0242(6) Uani 1 1 d . . .
H9A H 0.6838 0.9934 0.0791 0.029 Uiso 1 1 calc R . .
H9B H 0.5884 0.9967 0.0332 0.029 Uiso 1 1 calc R . .
C10 C 0.7516(4) 0.8851(2) 0.03611(10) 0.0254(7) Uani 1 1 d . . .
H10A H 0.8333 0.9246 0.0206 0.030 Uiso 1 1 calc R . .
H10B H 0.6976 0.8439 0.0138 0.030 Uiso 1 1 calc R . .
C11 C 0.8351(3) 0.8192(2) 0.06959(10) 0.0218(6) Uani 1 1 d . . .
H11A H 0.9287 0.7879 0.0554 0.026 Uiso 1 1 calc R . .
H11B H 0.8742 0.8590 0.0947 0.026 Uiso 1 1 calc R . .
O3 O -0.0561(3) 0.80429(17) 0.17655(8) 0.0263(5) Uani 1 1 d . . .
HO3C H 0.038(4) 0.833(3) 0.1822(12) 0.039 Uiso 1 1 d . . .
HO3D H -0.044(5) 0.751(3) 0.1696(13) 0.039 Uiso 1 1 d . . .
Cl1 Cl 0.69023(8) 0.63239(5) -0.00729(2) 0.01774(15) Uani 1 1 d . . .
Cl2 Cl 0.56070(9) 1.08328(5) 0.15406(2) 0.02449(17) 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
Co 0.00919(16) 0.01080(17) 0.01011(17) -0.00004(14) 0.00036(13) -0.00042(13)
N1 0.0158(11) 0.0154(11) 0.0120(11) 0.0002(9) -0.0012(8) -0.0013(9)
N2 0.0123(10) 0.0093(10) 0.0159(11) -0.0013(8) 0.0010(8) -0.0003(8)
N3 0.0136(11) 0.0117(11) 0.0125(11) -0.0014(8) -0.0008(8) -0.0015(8)
N4 0.0157(11) 0.0149(11) 0.0191(12) 0.0031(9) -0.0028(9) -0.0013(9)
N5 0.0124(10) 0.0139(11) 0.0138(11) 0.0005(8) -0.0002(8) 0.0005(9)
O1 0.0125(9) 0.0177(10) 0.0134(9) -0.0011(7) 0.0005(7) 0.0021(7)
O2 0.0164(10) 0.0272(11) 0.0202(10) -0.0045(9) 0.0071(8) 0.0027(8)
C1 0.0143(13) 0.0221(15) 0.0179(14) 0.0011(11) -0.0008(10) -0.0054(11)
C2 0.0269(15) 0.0147(13) 0.0211(15) 0.0003(11) -0.0021(12) -0.0072(11)
C3 0.0197(13) 0.0129(13) 0.0156(13) -0.0033(10) 0.0011(10) 0.0019(11)
C4 0.0126(12) 0.0142(13) 0.0164(13) 0.0014(10) 0.0004(10) 0.0003(10)
C5 0.0356(17) 0.0213(15) 0.0187(15) 0.0053(12) 0.0008(13) 0.0005(13)
C6 0.0184(13) 0.0189(13) 0.0118(13) -0.0001(10) -0.0016(10) 0.0016(11)
C7 0.0154(13) 0.0140(13) 0.0148(13) -0.0033(10) 0.0019(10) 0.0013(10)
C8 0.0139(13) 0.0111(12) 0.0179(14) 0.0011(10) 0.0032(10) 0.0003(10)
C9 0.0270(16) 0.0214(15) 0.0242(16) 0.0038(12) 0.0044(12) -0.0033(12)
C10 0.0335(17) 0.0202(15) 0.0224(15) 0.0045(12) 0.0109(13) -0.0027(13)
C11 0.0169(14) 0.0247(15) 0.0238(15) 0.0000(12) 0.0074(11) -0.0067(12)
O3 0.0197(11) 0.0254(12) 0.0337(13) -0.0056(10) -0.0079(9) 0.0051(9)
Cl1 0.0196(3) 0.0181(3) 0.0155(3) 0.0004(2) 0.0017(2) 0.0004(3)
Cl2 0.0238(4) 0.0177(3) 0.0320(4) 0.0005(3) -0.0015(3) 0.0030(3)

_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
Co O1 1.9126(18) . ?
Co N3 1.938(2) . ?
Co N5 1.959(2) . ?
Co N2 1.970(2) . ?
Co N4 1.982(2) . ?
Co N1 1.994(2) . ?
N1 C1 1.489(3) . ?
N2 C4 1.283(3) . ?
N2 C3 1.478(3) . ?
N3 C7 1.480(3) . ?
N4 C9 1.482(3) . ?
N5 C11 1.486(3) . ?
O1 C8 1.298(3) . ?
O2 C8 1.228(3) . ?
C1 C2 1.526(4) . ?
C2 C3 1.525(4) . ?
C4 C6 1.501(4) . ?
C4 C5 1.507(4) . ?
C6 C7 1.522(4) . ?
C7 C8 1.526(4) . ?
C9 C10 1.505(4) . ?
C10 C11 1.526(4) . ?

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
O1 Co N3 84.29(8) . . ?
O1 Co N5 176.99(9) . . ?
N3 Co N5 92.73(9) . . ?
O1 Co N2 91.77(8) . . ?
N3 Co N2 90.47(9) . . ?
N5 Co N2 88.67(9) . . ?
O1 Co N4 84.56(9) . . ?
N3 Co N4 90.47(9) . . ?
N5 Co N4 95.07(9) . . ?
N2 Co N4 176.10(9) . . ?
O1 Co N1 89.20(8) . . ?
N3 Co N1 173.48(9) . . ?
N5 Co N1 93.78(9) . . ?
N2 Co N1 89.46(9) . . ?
N4 Co N1 89.18(9) . . ?
C1 N1 Co 113.86(16) . . ?
C4 N2 C3 118.9(2) . . ?
C4 N2 Co 127.41(18) . . ?
C3 N2 Co 113.72(16) . . ?
C7 N3 Co 105.04(15) . . ?
C9 N4 Co 123.48(18) . . ?
C11 N5 Co 119.78(17) . . ?
C8 O1 Co 113.69(16) . . ?
N1 C1 C2 111.8(2) . . ?
C3 C2 C1 112.5(2) . . ?
N2 C3 C2 111.6(2) . . ?
N2 C4 C6 122.2(2) . . ?
N2 C4 C5 124.2(2) . . ?
C6 C4 C5 113.6(2) . . ?
C4 C6 C7 117.5(2) . . ?
N3 C7 C6 110.1(2) . . ?
N3 C7 C8 107.1(2) . . ?
C6 C7 C8 109.7(2) . . ?
O2 C8 O1 124.0(2) . . ?
O2 C8 C7 121.3(2) . . ?
O1 C8 C7 114.6(2) . . ?
N4 C9 C10 113.0(2) . . ?
C9 C10 C11 113.8(2) . . ?
N5 C11 C10 111.2(2) . . ?

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
O1 Co N1 C1 -53.90(18) . . . . ?
N3 Co N1 C1 -51.5(9) . . . . ?
N5 Co N1 C1 126.50(18) . . . . ?
N2 Co N1 C1 37.87(18) . . . . ?
N4 Co N1 C1 -138.47(18) . . . . ?
O1 Co N2 C4 -60.1(2) . . . . ?
N3 Co N2 C4 24.2(2) . . . . ?
N5 Co N2 C4 117.0(2) . . . . ?
N4 Co N2 C4 -79.6(14) . . . . ?
N1 Co N2 C4 -149.2(2) . . . . ?
O1 Co N2 C3 119.19(17) . . . . ?
N3 Co N2 C3 -156.51(17) . . . . ?
N5 Co N2 C3 -63.79(17) . . . . ?
N4 Co N2 C3 99.6(14) . . . . ?
N1 Co N2 C3 30.00(17) . . . . ?
O1 Co N3 C7 33.34(15) . . . . ?
N5 Co N3 C7 -147.08(16) . . . . ?
N2 Co N3 C7 -58.39(16) . . . . ?
N4 Co N3 C7 117.82(16) . . . . ?
N1 Co N3 C7 30.9(9) . . . . ?
O1 Co N4 C9 153.8(2) . . . . ?
N3 Co N4 C9 69.6(2) . . . . ?
N5 Co N4 C9 -23.2(2) . . . . ?
N2 Co N4 C9 173.5(13) . . . . ?
N1 Co N4 C9 -116.9(2) . . . . ?
O1 Co N5 C11 -52.9(17) . . . . ?
N3 Co N5 C11 -60.9(2) . . . . ?
N2 Co N5 C11 -151.3(2) . . . . ?
N4 Co N5 C11 29.8(2) . . . . ?
N1 Co N5 C11 119.3(2) . . . . ?
N3 Co O1 C8 -19.95(17) . . . . ?
N5 Co O1 C8 -27.9(17) . . . . ?
N2 Co O1 C8 70.34(18) . . . . ?
N4 Co O1 C8 -110.97(18) . . . . ?
N1 Co O1 C8 159.78(18) . . . . ?
Co N1 C1 C2 -73.1(2) . . . . ?
N1 C1 C2 C3 30.1(3) . . . . ?
C4 N2 C3 C2 103.6(3) . . . . ?
Co N2 C3 C2 -75.8(2) . . . . ?
C1 C2 C3 N2 44.4(3) . . . . ?
C3 N2 C4 C6 179.4(2) . . . . ?
Co N2 C4 C6 -1.4(4) . . . . ?
C3 N2 C4 C5 0.8(4) . . . . ?
Co N2 C4 C5 180.0(2) . . . . ?
N2 C4 C6 C7 9.3(4) . . . . ?
C5 C4 C6 C7 -172.0(2) . . . . ?
Co N3 C7 C6 79.5(2) . . . . ?
Co N3 C7 C8 -39.7(2) . . . . ?
C4 C6 C7 N3 -52.2(3) . . . . ?
C4 C6 C7 C8 65.4(3) . . . . ?
Co O1 C8 O2 -177.2(2) . . . . ?
Co O1 C8 C7 0.4(3) . . . . ?
N3 C7 C8 O2 -155.3(2) . . . . ?
C6 C7 C8 O2 85.3(3) . . . . ?
N3 C7 C8 O1 27.0(3) . . . . ?
C6 C7 C8 O1 -92.4(3) . . . . ?
Co N4 C9 C10 41.3(3) . . . . ?
N4 C9 C10 C11 -63.5(3) . . . . ?
Co N5 C11 C10 -55.2(3) . . . . ?
C9 C10 C11 N5 71.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1  0.92 2.40 3.318(2) 179.1 4_465
N1 H1B Cl1  0.92 2.66 3.547(2) 161.8 .
N3 H3A O3  0.92 1.90 2.813(3) 169.1 1_655
N3 H3B Cl2  0.92 2.33 3.187(2) 154.0 .
N4 H4A Cl1  0.92 2.44 3.340(2) 165.2 4_465
N4 H4B Cl2  0.92 2.78 3.461(2) 131.5 .
N5 H5A Cl2  0.92 2.58 3.489(2) 169.7 8_755
N5 H5B Cl1  0.92 2.33 3.222(2) 162.7 .
O3 H3C O2  0.89(4) 1.90(4) 2.776(3) 166(3) .
O3 H3D Cl2  0.77(4) 2.35(4) 3.107(2) 168(4) 8_655

_diffrn_measured_fraction_theta_max    0.955
_diffrn_reflns_theta_full              26.00
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.692
_refine_diff_density_min   -0.503
_refine_diff_density_rms    0.094