#------------------------------------------------------------------------------
#$Date: 2017-09-19 08:31:49 +0200 (mar 19 de sep de 2017) $
#$Revision: 201022 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/92/7229207.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7229207
loop_
_publ_author_name
'Pereira, Jorge F. B.'
'Barber, Patrick S.'
'Kelley, Steven Paul'
'Berton, Paula'
'Rogers, Robin D.'
_publ_section_title
;
 Double Salt Ionic Liquids Based on 1-Ethyl-3-Methylimidazolium Acetate
 and Hydroxyl-Functionalized Ammonium Acetates: Strong Effects of Weak
 Interactions
;
_journal_name_full               'Phys. Chem. Chem. Phys.'
_journal_paper_doi               10.1039/C7CP05710E
_journal_year                    2017
_chemical_formula_moiety         'C2 H8 N +, C2 H3 O2 -'
_chemical_formula_sum            'C4 H11 N O2'
_chemical_formula_weight         105.14
_chemical_name_systematic        'Ethylammonium acetate'
_chemical_properties_physical    Deliquescent
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   6.9335(6)
_cell_length_b                   6.9335(6)
_cell_length_c                   10.7367(11)
_cell_measurement_reflns_used    7272
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.90
_cell_measurement_theta_min      3.39
_cell_volume                     447.00(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15721
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.123
_diffrn_reflns_theta_min         3.393
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             174
_exptl_crystal_recrystallization_method
'Crystallized spontaneously from reaction mixture'
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.0342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                1956
_reflns_number_total             2239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp05710e2.cif
_cod_data_source_block           NH3EtOAc
_cod_original_cell_volume        446.99(9)
_cod_database_code               7229207
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_file
; 
  
    s1.res created by SHELXL-2014/7 
  
  
TITL s1 in P3(2) 
CELL 0.71073   6.93345   6.93345  10.73670  90.0000  90.0000 120.0000 
ZERR    3.00   0.00060   0.00060   0.00110   0.0000   0.0000   0.0000 
LATT -1 
SYMM -Y, X-Y, 0.66667+Z 
SYMM -X+Y, -X, 0.33333+Z 
SFAC C H N O 
UNIT 12 33 3 6 
TEMP -173 
SIZE 0.15 0.21 1.00 
  
L.S. 10 
ACTA 
FMAP 2 
PLAN 20 
  
WGHT    0.051000    0.034200 
FVAR       0.50056 
N1    3    0.123436    0.725519    0.047516    11.00000    0.02078    0.01463 = 
         0.01341   -0.00016   -0.00043    0.01086 
O1    4    0.304411    0.469279   -0.028934    11.00000    0.03390    0.02038 = 
         0.01481    0.00169    0.00146    0.01919 
C3    1    0.314831    0.313514    0.026636    11.00000    0.01133    0.01281 = 
         0.01386    0.00032    0.00094    0.00535 
O2    4    0.320470    0.159152   -0.030936    11.00000    0.03206    0.01627 = 
         0.01695    0.00005    0.00312    0.01422 
C4    1    0.327873    0.319454    0.167665    11.00000    0.02192    0.02073 = 
         0.01179   -0.00072   -0.00080    0.01187 
AFIX 137 
H4A   2    0.254484    0.166902    0.200054    11.00000   -1.50000 
H4B   2    0.253214    0.397077    0.200487    11.00000   -1.50000 
H4C   2    0.484352    0.398222    0.193606    11.00000   -1.50000 
AFIX   0 
C1    1   -0.098026    0.634800   -0.013165    11.00000    0.01922    0.02072 = 
         0.01942    0.00120   -0.00024    0.01043 
AFIX  23 
H1E   2   -0.172146    0.716037    0.017624    11.00000   -1.20000 
H1D   2   -0.192512    0.475802    0.009232    11.00000   -1.20000 
AFIX   0 
C2    1   -0.074759    0.657137   -0.153172    11.00000    0.03103    0.02865 = 
         0.01731   -0.00504   -0.00705    0.01650 
AFIX 137 
H2A   2    0.024544    0.813648   -0.175197    11.00000   -1.50000 
H2B   2   -0.221466    0.605161   -0.190709    11.00000   -1.50000 
H2C   2   -0.012270    0.567083   -0.184384    11.00000   -1.50000 
AFIX   0 
H1A   2    0.114634    0.719971    0.135722    11.00000    0.03430 
H1B   2    0.189533    0.656283    0.023833    11.00000    0.02304 
H1C   2    0.203106    0.860980    0.029492    11.00000    0.02488 
  
HKLF 4 
  
REM  s1 in P3(2) 
REM R1 =  0.0425 for    1956 Fo > 4sig(Fo)  and  0.0553 for all    2239 data 
REM     78 parameters refined using      1 restraints 
  
END 
  
WGHT      0.0443      0.0335 
  
REM Highest difference peak  0.226,  deepest hole -0.341,  1-sigma level  0.064 
Q1    1   0.3256  0.3154  0.0989  11.00000  0.05    0.23 
Q2    1  -0.0879  0.6497 -0.0832  11.00000  0.05    0.22 
Q3    1   0.1597  0.9257  0.1927  11.00000  0.05    0.17 
Q4    1   0.0095  0.0126  0.2361  11.00000  0.05    0.17 
Q5    1  -0.3197  0.6858 -0.2369  11.00000  0.05    0.17 
Q6    1   0.3133  0.4741 -0.0980  11.00000  0.05    0.17 
Q7    1   0.6943  0.6626  0.1671  11.00000  0.05    0.17 
Q8    1   0.3739  0.6550  0.0534  11.00000  0.05    0.16 
Q9    1  -0.1736  0.7109 -0.1833  11.00000  0.05    0.16 
Q10   1   0.2953  0.6863  0.1252  11.00000  0.05    0.15 
Q11   1   0.3399  0.1790 -0.1082  11.00000  0.05    0.15 
Q12   1  -0.2709  0.3314 -0.0605  11.00000  0.05    0.15 
Q13   1  -0.0136  0.9953 -0.1526  11.00000  0.05    0.15 
Q14   1   0.3170  0.6595 -0.1167  11.00000  0.05    0.15 
Q15   1   0.2324  0.1303 -0.1133  11.00000  0.05    0.15 
Q16   1  -0.3727  0.6430  0.0545  11.00000  0.05    0.15 
Q17   1   0.6192  0.3235  0.1086  11.00000  0.05    0.15 
Q18   1  -0.2238  0.7723 -0.0519  11.00000  0.05    0.15 
Q19   1  -0.0134  0.9882 -0.0127  11.00000  0.05    0.15 
Q20   1   0.3200  0.6047 -0.0451  11.00000  0.05    0.14 
;
_shelx_res_checksum              49811
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.1234(2) 0.7255(2) 0.04752(12) 0.0154(3) Uani 1 1 d . .
O1 O 0.3044(2) 0.46928(19) -0.02893(11) 0.0205(3) Uani 1 1 d . .
C3 C 0.3148(2) 0.3135(2) 0.02664(14) 0.0130(3) Uani 1 1 d . .
O2 O 0.3205(2) 0.15915(19) -0.03094(11) 0.0208(3) Uani 1 1 d . .
C4 C 0.3279(3) 0.3195(3) 0.16766(16) 0.0176(3) Uani 1 1 d . .
H4A H 0.2545 0.1669 0.2001 0.026 Uiso 1 1 calc R U
H4B H 0.2532 0.3971 0.2005 0.026 Uiso 1 1 calc R U
H4C H 0.4844 0.3982 0.1936 0.026 Uiso 1 1 calc R U
C1 C -0.0980(3) 0.6348(3) -0.01317(15) 0.0196(3) Uani 1 1 d . .
H1E H -0.1721 0.7160 0.0176 0.024 Uiso 1 1 calc R U
H1D H -0.1925 0.4758 0.0092 0.024 Uiso 1 1 calc R U
C2 C -0.0748(3) 0.6571(3) -0.15317(18) 0.0250(4) Uani 1 1 d . .
H2A H 0.0245 0.8136 -0.1752 0.037 Uiso 1 1 calc R U
H2B H -0.2215 0.6052 -0.1907 0.037 Uiso 1 1 calc R U
H2C H -0.0123 0.5671 -0.1844 0.037 Uiso 1 1 calc R U
H1A H 0.115(4) 0.720(5) 0.136(3) 0.034(7) Uiso 1 1 d . .
H1B H 0.190(4) 0.656(4) 0.024(2) 0.023(5) Uiso 1 1 d . .
H1C H 0.203(4) 0.861(4) 0.029(2) 0.025(6) Uiso 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 0.0208(6) 0.0146(6) 0.0134(6) -0.0002(5) -0.0004(5) 0.0109(5)
O1 0.0339(6) 0.0204(5) 0.0148(5) 0.0017(4) 0.0015(5) 0.0192(5)
C3 0.0113(6) 0.0128(6) 0.0139(7) 0.0003(5) 0.0009(5) 0.0054(5)
O2 0.0321(6) 0.0163(5) 0.0170(5) 0.0001(4) 0.0031(5) 0.0142(5)
C4 0.0219(7) 0.0207(7) 0.0118(6) -0.0007(5) -0.0008(5) 0.0119(6)
C1 0.0192(7) 0.0207(7) 0.0194(8) 0.0012(6) -0.0002(6) 0.0104(6)
C2 0.0310(8) 0.0286(9) 0.0173(8) -0.0050(6) -0.0071(7) 0.0165(7)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C3 O1 122.34(15)
O2 C3 C4 119.26(13)
O1 C3 C4 118.37(13)
N1 C1 C2 110.95(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.487(2)
O1 C3 1.2671(19)
C3 O2 1.2534(18)
C3 C4 1.516(2)
C1 C2 1.512(3)
