# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_wj1045
#TrackingRef 'Final.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-propylammonium oxalate
;
_chemical_name_common            (pa)2(ox)
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 N2 O4'
_chemical_formula_weight         208.26

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   11.0906(3)
_cell_length_b                   14.6981(5)
_cell_length_c                   7.6029(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1239.35(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    4563
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      26.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.898

_exptl_absorpt_correction_T_max  0.995

_exptl_absorpt_process_details   
;

multi-scan from symmetry-related measurements

Sortav (Blessing 1995)

;

_diffrn_ambient_temperature      250(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6064
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         26.04
_reflns_number_total             1310
_reflns_number_gt                856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. Hydrogen atoms were placed
in riding positions calculated based on the hybridization mode of the
parent carbon or nitrogen atom.
;

_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^)+(0.1302P)^2^+0.8975P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(7)
_refine_ls_number_reflns         1310
_refine_ls_number_parameters     130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2622
_refine_ls_wR_factor_gt          0.2215
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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 0.0775(3) 0.9618(3) 0.7275(11) 0.0580(12) Uani 1 1 d . . .
H1N H 0.1013 0.9872 0.8294 0.070 Uiso 1 1 calc R . .
H2N H -0.0014 0.9731 0.7105 0.070 Uiso 1 1 calc R . .
H3N H 0.1203 0.9858 0.6381 0.070 Uiso 1 1 calc R . .
C1 C 0.2554(10) 0.7491(8) 0.719(3) 0.182(7) Uani 1 1 d . . .
H1C H 0.3421 0.7401 0.7165 0.273 Uiso 1 1 calc R . .
H1D H 0.2212 0.7297 0.6072 0.273 Uiso 1 1 calc R . .
H1E H 0.2206 0.7135 0.8132 0.273 Uiso 1 1 calc R . .
C2 C 0.2301(7) 0.8411(6) 0.745(2) 0.121(4) Uani 1 1 d . . .
H2A H 0.2740 0.8769 0.6576 0.146 Uiso 1 1 calc R . .
H2B H 0.2603 0.8588 0.8616 0.146 Uiso 1 1 calc R . .
C3 C 0.0971(5) 0.8652(5) 0.7344(19) 0.0885(18) Uani 1 1 d . . .
H3A H 0.0624 0.8370 0.6291 0.106 Uiso 1 1 calc R . .
H3B H 0.0553 0.8402 0.8371 0.106 Uiso 1 1 calc R . .
C5 C 0.4645(11) 0.6985(5) 0.242(3) 0.180(6) Uani 1 1 d . . .
H5A H 0.4319 0.6613 0.3357 0.271 Uiso 1 1 calc R . .
H5B H 0.5441 0.6765 0.2102 0.271 Uiso 1 1 calc R . .
H5C H 0.4119 0.6949 0.1399 0.271 Uiso 1 1 calc R . .
C6 C 0.4735(10) 0.8003(8) 0.3049(16) 0.126(3) Uani 1 1 d . . .
H6A H 0.3939 0.8284 0.2925 0.151 Uiso 1 1 calc R . .
H6B H 0.4938 0.8004 0.4304 0.151 Uiso 1 1 calc R . .
C7 C 0.5497(8) 0.8493(6) 0.225(3) 0.165(6) Uani 1 1 d . . .
H7A H 0.5414 0.8333 0.1003 0.198 Uiso 1 1 calc R . .
H7B H 0.6288 0.8265 0.2614 0.198 Uiso 1 1 calc R . .
C8 C 0.7516(5) 0.9821(5) -0.3707(9) 0.049(2) Uani 1 1 d . . .
C9 C 0.7515(6) 0.9810(6) -0.1662(8) 0.053(2) Uani 1 1 d . . .
O10 O 0.6517(6) 0.9918(5) -0.0936(5) 0.082(2) Uani 1 1 d . . .
O11 O 0.6541(6) 0.9886(5) -0.4429(5) 0.083(2) Uani 1 1 d . . .
N12 N 0.5601(3) 0.9481(3) 0.2284(11) 0.0549(10) Uani 1 1 d . . .
H4N H 0.4872 0.9731 0.2093 0.066 Uiso 1 1 calc R . .
H5N H 0.6115 0.9663 0.1439 0.066 Uiso 1 1 calc R . .
H6N H 0.5880 0.9658 0.3341 0.066 Uiso 1 1 calc R . .
O14 O 0.8493(6) 0.9730(4) -0.4440(5) 0.0658(16) Uani 1 1 d . . .
O13 O 0.8513(6) 0.9727(5) -0.0916(5) 0.0779(19) 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
N1 0.0363(17) 0.102(3) 0.0356(19) -0.010(4) 0.001(4) 0.0089(18)
C1 0.171(10) 0.159(10) 0.22(2) -0.083(16) -0.011(14) 0.068(8)
C2 0.105(5) 0.113(6) 0.146(9) -0.052(9) -0.001(8) 0.028(4)
C3 0.079(4) 0.105(5) 0.082(4) 0.013(7) 0.003(6) 0.012(3)
C5 0.234(12) 0.063(4) 0.244(17) -0.009(13) 0.045(17) -0.018(6)
C6 0.158(9) 0.134(8) 0.086(6) -0.015(6) 0.012(7) 0.001(7)
C7 0.105(6) 0.099(6) 0.290(19) 0.052(13) 0.059(12) -0.018(5)
C8 0.035(5) 0.081(5) 0.030(4) 0.001(4) -0.005(3) 0.004(3)
C9 0.045(5) 0.087(6) 0.028(4) 0.003(4) -0.004(3) -0.004(4)
O10 0.033(4) 0.178(6) 0.036(3) 0.009(4) 0.010(3) 0.008(4)
O11 0.048(4) 0.168(6) 0.031(3) -0.004(4) -0.004(3) 0.016(4)
N12 0.0390(17) 0.089(3) 0.0371(18) -0.001(4) 0.002(4) -0.0036(17)
O14 0.042(4) 0.125(5) 0.031(2) 0.013(3) 0.005(3) 0.014(3)
O13 0.041(4) 0.154(6) 0.038(3) -0.004(4) -0.010(3) 0.009(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
N1 C3 1.438(8) . ?
N1 H1N 0.9000 . ?
N1 H2N 0.9000 . ?
N1 H3N 0.9000 . ?
C1 C2 1.396(13) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C2 C3 1.519(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C5 C6 1.575(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.266(14) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 N12 1.456(10) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 O11 1.216(8) . ?
C8 O14 1.226(8) . ?
C8 C9 1.555(6) . ?
C9 O10 1.247(8) . ?
C9 O13 1.249(8) . ?
N12 H4N 0.9000 . ?
N12 H5N 0.9000 . ?
N12 H6N 0.9000 . ?

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
C3 N1 H1N 109.5 . . ?
C3 N1 H2N 109.5 . . ?
H1N N1 H2N 109.5 . . ?
C3 N1 H3N 109.5 . . ?
H1N N1 H3N 109.5 . . ?
H2N N1 H3N 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C1 C2 C3 114.4(8) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N1 C3 C2 112.3(6) . . ?
N1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C5 115.9(12) . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 N12 127.7(13) . . ?
C6 C7 H7A 105.4 . . ?
N12 C7 H7A 105.4 . . ?
C6 C7 H7B 105.4 . . ?
N12 C7 H7B 105.4 . . ?
H7A C7 H7B 106.0 . . ?
O11 C8 O14 126.1(8) . . ?
O11 C8 C9 116.9(7) . . ?
O14 C8 C9 117.0(7) . . ?
O10 C9 O13 126.7(7) . . ?
O10 C9 C8 116.2(7) . . ?
O13 C9 C8 117.0(7) . . ?
C7 N12 H4N 109.5 . . ?
C7 N12 H5N 109.5 . . ?
H4N N12 H5N 109.5 . . ?
C7 N12 H6N 109.5 . . ?
H4N N12 H6N 109.5 . . ?
H5N N12 H6N 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
C1 C2 C3 N1 -168.3(17) . . . . ?
C5 C6 C7 N12 166.0(16) . . . . ?
O11 C8 C9 O10 -3.7(15) . . . . ?
O14 C8 C9 O10 178.8(6) . . . . ?
O11 C8 C9 O13 178.8(6) . . . . ?
O14 C8 C9 O13 1.3(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_vrf_PLAT241_wj1045              
;
PROBLEM: Check High Ueq as Compared to Neighbors for C7
RESPONSE: This atom is a part of a terminal hydrocarbon
chain and its neighbor is a highly hydrogen-bonded
nitrogen atom which, therefore, exhibits much lower thermal
motion. Thermal parameters of C7 are comparable to those
of C5 in the same chain.
Furthermore, the structure has been collected
at 250 K - it is not unusual to observe high thermal
parameters for hydrocarbon chains in such cases. Attempts
to model disorder did not yield a better structural model.
;

_database_code_depnum_ccdc_archive 'CCDC 933546'