# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2001

data_mb

_database_code_CSD	166637


_audit_creation_method        SHELXL-97

loop_
_publ_author_name

'Chuburu, F.'
'Handel, H.'
'Le Baccon, M.'

_publ_contact_author_name     	'Dr H Handel'  
_publ_contact_author_address 
;
Chimie, Electrochimie Moleculaires et Chimie Analytique
Universite de Bretagne Occidentale
6 Av Victor Le Gorgeu
BP 809
Brest cedex
29285
FRANCE
;


_publ_contact_author_email       'HENRI.HANDEL@UNIV-BREST.FR'
_publ_contact_author_fax         '(33) 2 99 28 67 17'
_publ_contact_author_phone       '(33) 2 99 28 60 65'

_journal_coden_Cambridge    	440
_publ_requested_journal           'New J. Chem.'
_publ_requested_coeditor_name      ?
;
?
;

_publ_section_title		
;
Bis-aminals: efficient tools for bis-macrocycles synthesis
;

_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C15 H29 N4'
_chemical_formula_weight          265.42

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'

_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1

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

_cell_length_a                    8.7740(5)
_cell_length_b                    9.4790(5)
_cell_length_c                    10.8510(7)
_cell_angle_alpha                 80.211(2)
_cell_angle_beta                  82.197(2)
_cell_angle_gamma                 67.030(3)
_cell_volume                      816.41(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.22
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.080
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              294
_exptl_absorpt_coefficient_mu     0.066
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       293(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   Enraf_Nonius_KappaCCD
_diffrn_measurement_method        'Area detector scans (see text)'
_diffrn_detector_area_resol_mean  19.11
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3724
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.0516
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.91
_diffrn_reflns_theta_max          27.55
_reflns_number_total              3724
_reflns_number_gt                 2191
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Nonius (1999)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution     'SIR-97_(Altomare & al., 1998)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON_(Spek, 1998)'
_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^)+(0.1035P)^2^+0.0725P] 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        0.022(15)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3724
_refine_ls_number_parameters      170
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1103
_refine_ls_R_factor_gt            0.0613
_refine_ls_wR_factor_ref          0.2054
_refine_ls_wR_factor_gt           0.1736
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_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_symetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.31231(17) 0.11929(17) 0.78144(14) 0.0552(4) Uani 1 1 d . . .
N2 N 0.0068(2) 0.27585(19) 0.57733(16) 0.0626(4) Uani 1 1 d . . .
H2N H 0.035(2) 0.302(2) 0.6398(18) 0.050 Uiso 1 1 d . . .
N3 N -0.0998(2) 0.56771(19) 0.70651(18) 0.0686(5) Uani 1 1 d . . .
H3 H -0.073(2) 0.604(2) 0.6349(18) 0.050 Uiso 1 1 d . . .
N4 N 0.2636(2) 0.45250(19) 0.75989(16) 0.068 Uani 1 1 d . . .
H4 H 0.167(2) 0.4174(18) 0.7643(15) 0.050 Uiso 1 1 d . . .
C1 C -0.1505(2) 0.1119(2) 0.97139(17) 0.057 Uani 1 1 d . . .
H1 H -0.2523 0.1886 0.9516 0.068 Uiso 1 1 calc R . .
C2 C -0.0058(2) 0.1354(2) 0.92689(17) 0.0575(5) Uani 1 1 d . . .
H2 H -0.0114 0.2274 0.8774 0.069 Uiso 1 1 calc R . .
C3 C 0.1466(2) 0.0236(2) 0.95527(15) 0.0525(4) Uani 1 1 d . . .
C4 C 0.3049(2) 0.0528(3) 0.91332(19) 0.0679(6) Uani 1 1 d . . .
H4A H 0.3138 0.1225 0.9654 0.081 Uiso 1 1 calc R . .
H4B H 0.3992 -0.0440 0.9259 0.081 Uiso 1 1 calc R . .
C5 C 0.3445(3) 0.0003(2) 0.7014(2) 0.0689(6) Uani 1 1 d . . .
H5A H 0.2942 -0.0716 0.7434 0.083 Uiso 1 1 calc R . .
H5B H 0.4634 -0.0567 0.6917 0.083 Uiso 1 1 calc R . .
C6 C 0.2807(3) 0.0598(3) 0.5732(2) 0.0764(6) Uani 1 1 d . . .
H6A H 0.3330 -0.0212 0.5198 0.092 Uiso 1 1 calc R . .
H6B H 0.3137 0.1456 0.5374 0.092 Uiso 1 1 calc R . .
C7 C 0.0952(3) 0.1127(2) 0.5722(2) 0.0772(6) Uani 1 1 d . . .
H7A H 0.0702 0.0867 0.4966 0.093 Uiso 1 1 calc R . .
H7B H 0.0548 0.0562 0.6433 0.093 Uiso 1 1 calc R . .
C8 C -0.1725(3) 0.3140(3) 0.5985(2) 0.0766(6) Uani 1 1 d . . .
H8A H -0.1952 0.2596 0.6785 0.092 Uiso 1 1 calc R . .
H8B H -0.2079 0.2769 0.5338 0.092 Uiso 1 1 calc R . .
C9 C -0.2731(3) 0.4826(3) 0.5982(2) 0.0825(7) Uani 1 1 d . . .
H9A H -0.3889 0.4986 0.5955 0.099 Uiso 1 1 calc R . .
H9B H -0.2412 0.5370 0.5216 0.099 Uiso 1 1 calc R . .
C10 C -0.2596(3) 0.5554(3) 0.7065(2) 0.0831(7) Uani 1 1 d . . .
H10A H -0.3459 0.6579 0.7047 0.100 Uiso 1 1 calc R . .
H10B H -0.2793 0.4948 0.7841 0.100 Uiso 1 1 calc R . .
C11 C -0.1044(3) 0.6777(3) 0.7887(2) 0.0872(7) Uani 1 1 d . . .
H11A H -0.1205 0.6358 0.8752 0.105 Uiso 1 1 calc R . .
H11B H -0.1988 0.7732 0.7713 0.105 Uiso 1 1 calc R . .
C12 C 0.0504(4) 0.7129(3) 0.7730(2) 0.0833(7) Uani 1 1 d . . .
H12A H 0.0271 0.8045 0.8122 0.100 Uiso 1 1 calc R . .
H12B H 0.0760 0.7375 0.6841 0.100 Uiso 1 1 calc R . .
C13 C 0.2025(3) 0.5868(3) 0.8263(2) 0.0826(7) Uani 1 1 d . . .
H13A H 0.2894 0.6270 0.8222 0.099 Uiso 1 1 calc R . .
H13B H 0.1762 0.5559 0.9138 0.099 Uiso 1 1 calc R . .
C14 C 0.4044(3) 0.3277(3) 0.8144(2) 0.0749(6) Uani 1 1 d . . .
H14A H 0.3795 0.3081 0.9041 0.090 Uiso 1 1 calc R . .
H14B H 0.5000 0.3574 0.8014 0.090 Uiso 1 1 calc R . .
C15 C 0.4449(2) 0.1828(2) 0.7563(2) 0.0697(6) Uani 1 1 d . . .
H15A H 0.4652 0.2046 0.6663 0.084 Uiso 1 1 calc R . .
H15B H 0.5464 0.1049 0.7881 0.084 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
N1 0.0475(8) 0.0601(9) 0.0563(9) -0.0014(7) 0.0027(6) -0.0229(7)
N2 0.0731(11) 0.0660(10) 0.0587(10) -0.0065(8) -0.0093(8) -0.0362(8)
N3 0.0689(11) 0.0623(10) 0.0658(11) -0.0069(8) 0.0036(8) -0.0184(8)
N4 0.080 0.065 0.066 -0.003 -0.013 -0.034
C1 0.046 0.067 0.053 -0.001 -0.006 -0.019
C2 0.0586(11) 0.0640(11) 0.0519(10) 0.0043(8) -0.0063(8) -0.0295(9)
C3 0.0498(9) 0.0699(11) 0.0418(9) -0.0022(8) -0.0056(7) -0.0282(8)
C4 0.0542(10) 0.0919(14) 0.0617(12) 0.0079(10) -0.0095(8) -0.0376(10)
C5 0.0673(12) 0.0584(11) 0.0728(13) -0.0065(10) 0.0044(10) -0.0188(9)
C6 0.0859(15) 0.0757(13) 0.0660(13) -0.0207(11) 0.0141(11) -0.0305(11)
C7 0.1064(18) 0.0682(13) 0.0697(14) -0.0050(10) -0.0196(12) -0.0439(12)
C8 0.0782(14) 0.1002(17) 0.0695(13) -0.0010(12) -0.0085(10) -0.0561(13)
C9 0.0597(12) 0.0979(17) 0.0851(16) 0.0117(13) -0.0155(11) -0.0309(12)
C10 0.0623(13) 0.0782(14) 0.0915(17) -0.0030(13) 0.0058(11) -0.0149(11)
C11 0.1017(18) 0.0687(13) 0.0767(15) -0.0199(12) -0.0005(13) -0.0144(13)
C12 0.129(2) 0.0605(12) 0.0660(14) -0.0090(10) -0.0135(13) -0.0390(13)
C13 0.118(2) 0.0704(13) 0.0703(14) -0.0062(11) -0.0190(13) -0.0448(13)
C14 0.0648(12) 0.0857(15) 0.0884(15) 0.0000(12) -0.0129(11) -0.0457(11)
C15 0.0472(10) 0.0763(13) 0.0796(14) 0.0048(11) 0.0061(9) -0.0262(9)

_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
N1 C5 1.457(3) . ?
N1 C4 1.466(2) . ?
N1 C15 1.481(2) . ?
N2 C7 1.442(3) . ?
N2 C8 1.464(3) . ?
N2 H2N 0.860(19) . ?
N3 C10 1.452(3) . ?
N3 C11 1.469(3) . ?
N3 H3 0.834(18) . ?
N4 C14 1.448(3) . ?
N4 C13 1.449(3) . ?
N4 H4 1.017(18) . ?
C1 C3 1.382(3) 2_557 ?
C1 C2 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C1 1.382(3) 2_557 ?
C3 C4 1.516(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.506(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.494(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.500(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.502(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C5 N1 C4 109.40(15) . . ?
C5 N1 C15 110.12(14) . . ?
C4 N1 C15 109.99(16) . . ?
C7 N2 C8 111.12(18) . . ?
C7 N2 H2N 109.8(12) . . ?
C8 N2 H2N 106.3(12) . . ?
C10 N3 C11 112.66(18) . . ?
C10 N3 H3 109.1(13) . . ?
C11 N3 H3 104.8(13) . . ?
C14 N4 C13 112.98(18) . . ?
C14 N4 H4 109.8(9) . . ?
C13 N4 H4 105.9(9) . . ?
C3 C1 C2 121.19(16) 2_557 . ?
C3 C1 H1 119.4 2_557 . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.50(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C1 118.31(16) . 2_557 ?
C2 C3 C4 120.67(17) . . ?
C1 C3 C4 120.93(16) 2_557 . ?
N1 C4 C3 113.18(15) . . ?
N1 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 114.74(17) . . ?
N1 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 114.23(17) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C6 114.30(19) . . ?
N2 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C9 114.17(18) . . ?
N2 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
N3 C10 C9 113.74(18) . . ?
N3 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N3 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 C12 113.35(19) . . ?
N3 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 116.2(2) . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
N4 C13 C12 112.60(19) . . ?
N4 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N4 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N4 C14 C15 110.85(18) . . ?
N4 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C15 C14 113.68(15) . . ?
N1 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
N1 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?

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
C3 C1 C2 C3 -0.2(3) 2_557 . . . ?
C1 C2 C3 C1 0.2(3) . . . 2_557 ?
C1 C2 C3 C4 -176.27(18) . . . . ?
C5 N1 C4 C3 -74.0(2) . . . . ?
C15 N1 C4 C3 164.92(16) . . . . ?
C2 C3 C4 N1 -46.9(3) . . . . ?
C1 C3 C4 N1 136.68(19) 2_557 . . . ?
C4 N1 C5 C6 153.39(17) . . . . ?
C15 N1 C5 C6 -85.6(2) . . . . ?
N1 C5 C6 C7 -74.0(2) . . . . ?
C8 N2 C7 C6 -169.92(18) . . . . ?
C5 C6 C7 N2 94.3(2) . . . . ?
C7 N2 C8 C9 -176.97(19) . . . . ?
N2 C8 C9 C10 -69.5(3) . . . . ?
C11 N3 C10 C9 163.0(2) . . . . ?
C8 C9 C10 N3 69.8(3) . . . . ?
C10 N3 C11 C12 -169.94(19) . . . . ?
N3 C11 C12 C13 -73.1(3) . . . . ?
C14 N4 C13 C12 -177.0(2) . . . . ?
C11 C12 C13 N4 67.2(3) . . . . ?
C13 N4 C14 C15 170.51(17) . . . . ?
C5 N1 C15 C14 168.01(17) . . . . ?
C4 N1 C15 C14 -71.3(2) . . . . ?
N4 C14 C15 N1 -64.6(2) . . . . ?

_diffrn_measured_fraction_theta_max    0.987
_diffrn_reflns_theta_full              27.55
_diffrn_measured_fraction_theta_full   0.987
_refine_diff_density_max    0.242
_refine_diff_density_min   -0.162
_refine_diff_density_rms    0.033