# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         1048
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Philip Jessop'
_publ_contact_author_email       jessop@chem.queensu.ca

_publ_section_title              
;
Design, Synthesis, and Solution Behaviour
of Small Polyamines as Switchable Water Additives

;
loop_
_publ_author_name
S.Mercer
T.Robert
D.Dixon
'Chein-Shun Chen'
'Z.Ghoshouni Rahami'
J.Harjani
S.Jahangiri
G.Peslherbe
P.Jessop

# Attachment '- pj35.cif'

data_pj35
_database_code_depnum_ccdc_archive 'CCDC 860228'
#TrackingRef '- pj35.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H33 N3'
_chemical_formula_weight         255.44

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           hexagonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   10.3969(4)
_cell_length_b                   10.3969(4)
_cell_length_c                   28.4886(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2666.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1256
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      180(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3702
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         26.95
_reflns_number_total             1296
_reflns_number_gt                974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0744P)^2^+1.1862P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1296
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.33583(12) -0.07062(12) 0.08636(4) 0.0440(4) Uani 1 1 d . . .
C1 C 0.53812(13) 0.35256(13) 0.09922(5) 0.0337(3) Uani 1 1 d . . .
H1A H 0.5348(15) 0.3528(15) 0.1336(5) 0.040 Uiso 1 1 d . . .
H1B H 0.4562(16) 0.3662(14) 0.0876(5) 0.040 Uiso 1 1 d . . .
C2 C 0.51724(12) 0.20305(12) 0.08324(4) 0.0319(3) Uani 1 1 d . . .
H2A H 0.5168(15) 0.2034(14) 0.0470(5) 0.038 Uiso 1 1 d . . .
C3 C 0.36913(13) 0.07701(13) 0.10118(5) 0.0372(4) Uani 1 1 d . A .
H3A H 0.3696 0.0802 0.1359 0.045 Uiso 1 1 calc R . .
H3B H 0.2886 0.0941 0.0901 0.045 Uiso 1 1 calc R . .
C4 C 0.21290(17) -0.18390(16) 0.11382(6) 0.0561(5) Uani 1 1 d . A .
H4A H 0.1934 -0.2825 0.1041 0.084 Uiso 1 1 calc R . .
H4B H 0.1239 -0.1761 0.1085 0.084 Uiso 1 1 calc R . .
H4C H 0.2388 -0.1692 0.1472 0.084 Uiso 1 1 calc R . .
C5 C 0.3011(2) -0.0955(2) 0.03709(7) 0.0820(7) Uani 1 1 d . A 1
H5A H 0.2755 -0.1971 0.0289 0.123 Uiso 1 1 calc R A 1
H5B H 0.3875 -0.0249 0.0187 0.123 Uiso 1 1 calc R A 1
H5C H 0.2167 -0.0813 0.0301 0.123 Uiso 1 1 calc R A 1

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 0.0318(6) 0.0285(6) 0.0643(8) -0.0115(5) -0.0021(5) 0.0096(5)
C1 0.0266(6) 0.0279(7) 0.0479(8) -0.0015(5) -0.0002(5) 0.0146(5)
C2 0.0270(6) 0.0275(6) 0.0399(7) -0.0022(5) -0.0007(5) 0.0126(5)
C3 0.0265(6) 0.0290(7) 0.0543(8) -0.0062(5) -0.0014(5) 0.0125(5)
C4 0.0387(8) 0.0314(8) 0.0844(11) -0.0042(7) -0.0012(7) 0.0072(6)
C5 0.0882(15) 0.0539(11) 0.0724(13) -0.0278(9) -0.0026(10) 0.0120(10)

_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 1.440(2) . ?
N1 C3 1.4570(15) . ?
N1 C4 1.4585(18) . ?
C1 C2 1.5228(16) 3_665 ?
C1 C2 1.5274(16) . ?
C1 H1A 0.981(15) . ?
C1 H1B 0.988(15) . ?
C2 C1 1.5228(16) 2_655 ?
C2 C3 1.5270(16) . ?
C2 H2A 1.031(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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 C3 112.19(13) . . ?
C5 N1 C4 109.76(12) . . ?
C3 N1 C4 110.24(11) . . ?
C2 C1 C2 112.50(11) 3_665 . ?
C2 C1 H1A 108.5(8) 3_665 . ?
C2 C1 H1A 108.3(8) . . ?
C2 C1 H1B 109.3(8) 3_665 . ?
C2 C1 H1B 110.6(8) . . ?
H1A C1 H1B 107.5(11) . . ?
C1 C2 C3 111.88(10) 2_655 . ?
C1 C2 C1 110.48(11) 2_655 . ?
C3 C2 C1 110.05(9) . . ?
C1 C2 H2A 107.7(7) 2_655 . ?
C3 C2 H2A 109.5(7) . . ?
C1 C2 H2A 107.1(7) . . ?
N1 C3 C2 114.43(10) . . ?
N1 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?

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
C2 C1 C2 C1 54.72(17) 3_665 . . 2_655 ?
C2 C1 C2 C3 178.77(9) 3_665 . . . ?
C5 N1 C3 C2 -71.06(16) . . . . ?
C4 N1 C3 C2 166.29(11) . . . . ?
C1 C2 C3 N1 -58.92(15) 2_655 . . . ?
C1 C2 C3 N1 177.85(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.95
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034