# Supplementary Material (ESI) for PCCP
# This journal is (c) the Owner Societies 2010


data_global

_journal_coden_Cambridge         1326

loop_
_publ_author_name
'Robin D Rogers'
'Katharina Bica'
'Mark Nieuwenhuyzen'
'Christiaan Rijksen'

_publ_contact_author_name        'Robin D Rogers'
_publ_contact_author_email       RDROGERS@AS.UA.EDU

_publ_section_title              
;
In Search of Pure Liquid Salt Forms of Aspirin: Ionic Liquid
Approaches with Acetylsalicylic Acid and Salicylic Acid
;

# Attachment 'TRAMSALB923855Gcif.cif'

data_tramsal
_database_code_depnum_ccdc_archive 'CCDC 762135'
#TrackingRef 'TRAMSALB923855Gcif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H31 N O5'
_chemical_formula_weight         401.49

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0510(10)
_cell_length_b                   9.834(3)
_cell_length_c                   12.765(4)
_cell_angle_alpha                74.69(2)
_cell_angle_beta                 89.45(2)
_cell_angle_gamma                76.56(2)
_cell_volume                     1064.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    38
_cell_measurement_theta_min      10.636
_cell_measurement_theta_max      25.121

_exptl_crystal_description       'irregular chunk'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Seimens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        2
_diffrn_reflns_number            4990
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2576
_reflns_number_gt                1921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens 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^)+(0.0631P)^2^+0.7834P] 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       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2576
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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
C1A C -0.1234(4) -0.0373(3) 0.2727(2) 0.0382(9) Uani 1 1 d . . .
H1AA H -0.2057 0.0082 0.3118 0.046 Uiso 1 1 calc R . .
C2A C 0.0253(4) -0.0663(3) 0.3383(2) 0.0497(10) Uani 1 1 d . . .
H2AA H 0.0413 0.0249 0.3459 0.060 Uiso 1 1 calc R . .
H2AB H 0.1087 -0.1077 0.2993 0.060 Uiso 1 1 calc R . .
C3A C 0.0258(5) -0.1692(3) 0.4505(2) 0.0571(11) Uani 1 1 d . . .
H3AA H -0.0545 -0.1261 0.4911 0.068 Uiso 1 1 calc R . .
H3AB H 0.1222 -0.1849 0.4898 0.068 Uiso 1 1 calc R . .
C4A C 0.0018(5) -0.3142(3) 0.4413(2) 0.0564(11) Uani 1 1 d . . .
H4AA H 0.0869 -0.3615 0.4067 0.068 Uiso 1 1 calc R . .
H4AB H -0.0031 -0.3768 0.5134 0.068 Uiso 1 1 calc R . .
C5A C -0.1450(4) -0.2902(3) 0.3747(2) 0.0497(10) Uani 1 1 d . . .
H5AA H -0.2302 -0.2558 0.4153 0.060 Uiso 1 1 calc R . .
H5AB H -0.1541 -0.3827 0.3653 0.060 Uiso 1 1 calc R . .
C6A C -0.1566(4) -0.1810(3) 0.2613(2) 0.0371(9) Uani 1 1 d . . .
C7A C -0.3148(4) -0.1564(3) 0.2097(2) 0.0400(9) Uani 1 1 d . . .
C8A C -0.4424(5) -0.0806(3) 0.2499(3) 0.0543(12) Uani 1 1 d . . .
H8AA H -0.4307 -0.0414 0.3072 0.065 Uiso 1 1 calc R . .
C9A C -0.5871(5) -0.0632(4) 0.2049(3) 0.0602(12) Uani 1 1 d . . .
H9AA H -0.6710 -0.0108 0.2316 0.072 Uiso 1 1 calc R . .
C10A C -0.6077(5) -0.1228(4) 0.1210(3) 0.0581(11) Uani 1 1 d . . .
H10A H -0.7048 -0.1116 0.0917 0.070 Uiso 1 1 calc R . .
C11A C -0.4818(5) -0.1993(3) 0.0815(2) 0.0493(11) Uani 1 1 d . . .
C12A C -0.3375(5) -0.2151(3) 0.1245(2) 0.0452(11) Uani 1 1 d . . .
H12A H -0.2539 -0.2657 0.0962 0.054 Uiso 1 1 calc R . .
O13A O -0.5130(3) -0.2579(3) -0.00011(19) 0.0722(9) Uani 1 1 d . . .
C14A C -0.3869(5) -0.3294(5) -0.0482(3) 0.0864(15) Uani 1 1 d . . .
H14A H -0.4227 -0.3698 -0.1010 0.130 Uiso 1 1 calc R . .
H14B H -0.3231 -0.4058 0.0071 0.130 Uiso 1 1 calc R . .
H14C H -0.3295 -0.2610 -0.0833 0.130 Uiso 1 1 calc R . .
C15A C -0.1254(4) 0.0646(3) 0.1593(2) 0.0442(9) Uani 1 1 d . . .
H15A H -0.0445 0.0199 0.1199 0.053 Uiso 1 1 calc R . .
H15B H -0.2211 0.0751 0.1208 0.053 Uiso 1 1 calc R . .
N16A N -0.1064(3) 0.2136(2) 0.15723(17) 0.0409(8) Uani 1 1 d . . .
H16A H -0.0067 0.2172 0.2002 0.085(13) Uiso 1 1 d R . .
C17A C -0.0934(5) 0.2967(3) 0.0427(2) 0.0629(12) Uani 1 1 d . . .
H17A H -0.0119 0.2423 0.0108 0.094 Uiso 1 1 calc R . .
H17B H -0.0728 0.3884 0.0421 0.094 Uiso 1 1 calc R . .
H17C H -0.1870 0.3129 0.0015 0.094 Uiso 1 1 calc R . .
C18A C -0.2325(5) 0.2956(3) 0.2087(3) 0.0632(11) Uani 1 1 d . . .
H18A H -0.2330 0.2452 0.2841 0.095 Uiso 1 1 calc R . .
H18B H -0.3279 0.3034 0.1725 0.095 Uiso 1 1 calc R . .
H18C H -0.2178 0.3909 0.2025 0.095 Uiso 1 1 calc R . .
O19A O -0.0419(3) -0.23303(19) 0.19398(15) 0.0458(7) Uani 1 1 d . . .
H19A H -0.0272 -0.3440 0.2122 0.124(16) Uiso 1 1 d R . .
O1B O 0.3447(3) 0.1262(2) 0.40941(19) 0.0627(8) Uani 1 1 d . . .
H1C H 0.2445 0.1454 0.3519 0.136(19) Uiso 1 1 d R . .
C1B C 0.3810(4) 0.2572(3) 0.3841(2) 0.0473(10) Uani 1 1 d . . .
C2B C 0.5096(5) 0.2699(4) 0.4345(3) 0.0580(11) Uani 1 1 d . . .
H2B H 0.5685 0.1900 0.4852 0.070 Uiso 1 1 calc R . .
C3B C 0.5506(5) 0.4001(4) 0.4099(3) 0.0633(11) Uani 1 1 d . . .
H3B H 0.6374 0.4078 0.4441 0.076 Uiso 1 1 calc R . .
C4B C 0.4639(5) 0.5204(4) 0.3343(3) 0.0601(12) Uani 1 1 d . . .
H4B H 0.4933 0.6079 0.3170 0.072 Uiso 1 1 calc R . .
C5B C 0.3342(5) 0.5094(3) 0.2853(3) 0.0518(11) Uani 1 1 d . . .
H5B H 0.2751 0.5906 0.2358 0.062 Uiso 1 1 calc R . .
C6B C 0.2896(4) 0.3783(3) 0.3086(2) 0.0414(9) Uani 1 1 d . . .
C7B C 0.1506(4) 0.3687(3) 0.2531(2) 0.0451(10) Uani 1 1 d . . .
O71B O 0.0584(3) 0.4786(2) 0.19728(19) 0.0629(8) Uani 1 1 d . . .
O72B O 0.1315(3) 0.2398(2) 0.26439(18) 0.0582(8) 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
C1A 0.045(3) 0.0337(13) 0.0394(13) -0.0131(10) 0.0015(14) -0.0123(13)
C2A 0.063(3) 0.0422(15) 0.0502(16) -0.0137(12) -0.0009(17) -0.0223(15)
C3A 0.073(3) 0.0514(17) 0.0482(16) -0.0092(13) -0.0103(17) -0.0220(17)
C4A 0.075(3) 0.0438(16) 0.0489(16) -0.0054(12) -0.0053(18) -0.0180(16)
C5A 0.067(3) 0.0344(13) 0.0500(16) -0.0082(11) 0.0024(17) -0.0190(15)
C6A 0.037(3) 0.0362(13) 0.0420(14) -0.0140(10) 0.0070(15) -0.0125(13)
C7A 0.038(3) 0.0367(13) 0.0506(15) -0.0151(11) 0.0083(16) -0.0152(14)
C8A 0.053(4) 0.0557(18) 0.066(2) -0.0319(15) 0.009(2) -0.0190(18)
C9A 0.047(4) 0.062(2) 0.080(2) -0.0352(17) 0.013(2) -0.0123(19)
C10A 0.048(3) 0.065(2) 0.0653(19) -0.0201(16) 0.0015(18) -0.0186(18)
C11A 0.046(4) 0.0573(18) 0.0509(16) -0.0209(13) -0.0004(18) -0.0177(17)
C12A 0.045(4) 0.0469(15) 0.0489(16) -0.0189(12) 0.0050(17) -0.0148(15)
O13A 0.060(2) 0.1016(19) 0.0695(15) -0.0484(14) -0.0045(13) -0.0179(15)
C14A 0.081(4) 0.113(3) 0.079(3) -0.062(2) -0.003(2) -0.009(3)
C15A 0.059(3) 0.0368(14) 0.0424(14) -0.0131(11) 0.0015(14) -0.0201(14)
N16A 0.047(2) 0.0346(11) 0.0439(12) -0.0111(9) 0.0025(12) -0.0145(11)
C17A 0.092(4) 0.0499(17) 0.0480(16) -0.0037(13) 0.0094(18) -0.0309(18)
C18A 0.065(4) 0.0482(17) 0.080(2) -0.0271(16) 0.015(2) -0.0107(17)
O19A 0.048(2) 0.0401(10) 0.0543(11) -0.0198(8) 0.0110(10) -0.0126(10)
O1B 0.068(2) 0.0436(11) 0.0721(14) -0.0058(10) -0.0021(13) -0.0165(11)
C1B 0.053(3) 0.0440(15) 0.0473(15) -0.0159(12) 0.0069(17) -0.0126(15)
C2B 0.054(4) 0.066(2) 0.0560(18) -0.0203(15) -0.0002(19) -0.0134(19)
C3B 0.054(3) 0.084(3) 0.065(2) -0.0373(19) 0.0004(19) -0.023(2)
C4B 0.066(4) 0.061(2) 0.069(2) -0.0294(16) 0.010(2) -0.0313(19)
C5B 0.059(4) 0.0454(16) 0.0576(17) -0.0192(13) 0.0013(18) -0.0188(16)
C6B 0.042(3) 0.0407(14) 0.0485(15) -0.0209(12) 0.0069(15) -0.0133(14)
C7B 0.048(3) 0.0391(15) 0.0525(16) -0.0195(12) 0.0036(16) -0.0112(15)
O71B 0.069(2) 0.0406(11) 0.0771(15) -0.0178(10) -0.0161(13) -0.0067(11)
O72B 0.058(2) 0.0392(11) 0.0803(15) -0.0138(10) -0.0114(13) -0.0189(11)

_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
C1A C2A 1.519(5) . ?
C1A C15A 1.526(4) . ?
C1A C6A 1.553(4) . ?
C2A C3A 1.520(4) . ?
C3A C4A 1.525(4) . ?
C4A C5A 1.521(5) . ?
C5A C6A 1.545(4) . ?
C6A O19A 1.431(3) . ?
C6A C7A 1.523(5) . ?
C7A C8A 1.394(5) . ?
C7A C12A 1.396(4) . ?
C8A C9A 1.389(5) . ?
C9A C10A 1.383(5) . ?
C10A C11A 1.382(5) . ?
C11A O13A 1.376(4) . ?
C11A C12A 1.381(5) . ?
O13A C14A 1.420(5) . ?
C15A N16A 1.508(3) . ?
N16A C18A 1.490(4) . ?
N16A C17A 1.494(3) . ?
O1B C1B 1.360(4) . ?
C1B C2B 1.381(5) . ?
C1B C6B 1.408(4) . ?
C2B C3B 1.372(5) . ?
C3B C4B 1.388(5) . ?
C4B C5B 1.375(5) . ?
C5B C6B 1.397(4) . ?
C6B C7B 1.484(5) . ?
C7B O71B 1.248(4) . ?
C7B O72B 1.289(3) . ?

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
C2A C1A C15A 112.7(3) . . ?
C2A C1A C6A 111.1(2) . . ?
C15A C1A C6A 108.6(2) . . ?
C1A C2A C3A 112.0(3) . . ?
C2A C3A C4A 110.5(2) . . ?
C5A C4A C3A 110.1(3) . . ?
C4A C5A C6A 114.4(3) . . ?
O19A C6A C7A 110.8(2) . . ?
O19A C6A C5A 111.1(2) . . ?
C7A C6A C5A 108.3(2) . . ?
O19A C6A C1A 104.9(2) . . ?
C7A C6A C1A 111.8(2) . . ?
C5A C6A C1A 109.8(2) . . ?
C8A C7A C12A 118.0(4) . . ?
C8A C7A C6A 120.8(3) . . ?
C12A C7A C6A 121.2(3) . . ?
C9A C8A C7A 120.5(3) . . ?
C10A C9A C8A 120.8(4) . . ?
C11A C10A C9A 119.0(4) . . ?
O13A C11A C12A 124.3(3) . . ?
O13A C11A C10A 115.1(4) . . ?
C12A C11A C10A 120.5(3) . . ?
C11A C12A C7A 121.2(3) . . ?
C11A O13A C14A 117.2(3) . . ?
N16A C15A C1A 114.9(2) . . ?
C18A N16A C17A 110.6(2) . . ?
C18A N16A C15A 112.6(3) . . ?
C17A N16A C15A 109.6(2) . . ?
O1B C1B C2B 118.6(3) . . ?
O1B C1B C6B 121.0(3) . . ?
C2B C1B C6B 120.3(3) . . ?
C3B C2B C1B 120.2(3) . . ?
C2B C3B C4B 120.6(4) . . ?
C5B C4B C3B 119.6(3) . . ?
C4B C5B C6B 121.1(3) . . ?
C5B C6B C1B 118.2(3) . . ?
C5B C6B C7B 120.0(3) . . ?
C1B C6B C7B 121.8(3) . . ?
O71B C7B O72B 121.8(3) . . ?
O71B C7B C6B 122.2(3) . . ?
O72B C7B C6B 116.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.687
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.687
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045