#------------------------------------------------------------------------------
#$Date: 2017-09-19 09:31:49 +0300 (Tue, 19 Sep 2017) $
#$Revision: 201022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/92/7229209.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_7229209
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_sum            'C6 H15 N O2'
_chemical_formula_weight         133.19
_chemical_properties_physical    Deliquescent
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_formula_units_Z            8
_cell_length_a                   10.9186(7)
_cell_length_b                   10.9186(7)
_cell_length_c                   13.3235(11)
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      74.24
_cell_measurement_theta_min      5.24
_cell_volume                     1588.37(19)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1290
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8487
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.369
_diffrn_reflns_theta_min         5.237
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
; 
 Flack x determined using 480 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0694
_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)+(0.1087P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                1352
_reflns_number_total             1605
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp05710e2.cif
_cod_data_source_block           NMe4OAc
_cod_original_cell_volume        1588.4(2)
_cod_database_code               7229209
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'
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
_atom_site_refinement_flags_occupancy
N2 N 0.5000 0.5000 0.7985(2) 0.0168(8) Uani 1 2 d S T P
N1 N 1.0000 0.5000 0.7714(3) 0.0210(8) Uani 1 2 d S T P
O1 O 0.3774(2) 0.2239(3) 0.94001(18) 0.0428(8) Uani 1 1 d . . .
O2 O 0.2210(3) 0.1939(3) 0.83626(17) 0.0452(8) Uani 1 1 d . . .
C4 C 0.4304(3) 0.4141(3) 0.7331(2) 0.0261(7) Uani 1 1 d . . .
H4A H 0.3734 0.4606 0.6909 0.039 Uiso 1 1 calc R U .
H4B H 0.3843 0.3565 0.7750 0.039 Uiso 1 1 calc R U .
H4C H 0.4876 0.3687 0.6904 0.039 Uiso 1 1 calc R U .
C3 C 0.4134(3) 0.5714(3) 0.8632(2) 0.0265(7) Uani 1 1 d . . .
H3A H 0.3556 0.6163 0.8206 0.040 Uiso 1 1 calc R U .
H3B H 0.4598 0.6295 0.9044 0.040 Uiso 1 1 calc R U .
H3C H 0.3682 0.5151 0.9069 0.040 Uiso 1 1 calc R U .
C5 C 0.2657(3) 0.2142(3) 0.9208(2) 0.0214(7) Uani 1 1 d . . .
C2 C 1.0796(3) 0.4230(3) 0.7062(3) 0.0354(9) Uani 1 1 d . . .
H2A H 1.1340 0.4758 0.6669 0.053 Uiso 1 1 calc R U .
H2B H 1.0284 0.3744 0.6608 0.053 Uiso 1 1 calc R U .
H2C H 1.1288 0.3680 0.7482 0.053 Uiso 1 1 calc R U .
C6 C 0.1788(4) 0.2329(6) 1.0066(3) 0.0544(13) Uani 1 1 d . . .
H6A H 0.1587 0.3201 1.0123 0.082 Uiso 1 1 calc R U .
H6B H 0.2172 0.2049 1.0690 0.082 Uiso 1 1 calc R U .
H6C H 0.1038 0.1859 0.9945 0.082 Uiso 1 1 calc R U .
C1 C 1.0780(3) 0.5808(4) 0.8355(3) 0.0396(9) Uani 1 1 d . . .
H1A H 1.0255 0.6347 0.8756 0.059 Uiso 1 1 calc R U .
H1B H 1.1314 0.6306 0.7926 0.059 Uiso 1 1 calc R U .
H1C H 1.1282 0.5302 0.8801 0.059 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N2 C4 108.4(3) 2_665 .
C4 N2 C3 109.34(18) 2_665 .
C4 N2 C3 110.02(18) . .
C4 N2 C3 110.02(18) 2_665 2_665
C4 N2 C3 109.34(18) . 2_665
C3 N2 C3 109.7(3) . 2_665
C2 N1 C2 108.7(4) 2_765 .
C2 N1 C1 109.4(2) 2_765 .
C2 N1 C1 109.5(2) . .
C2 N1 C1 109.5(2) 2_765 2_765
C2 N1 C1 109.4(2) . 2_765
C1 N1 C1 110.3(4) . 2_765
O2 C5 O1 125.5(3) . .
O2 C5 C6 117.7(3) . .
O1 C5 C6 116.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C4 1.488(3) 2_665
N2 C4 1.489(3) .
N2 C3 1.498(4) .
N2 C3 1.498(4) 2_665
N1 C2 1.488(4) 2_765
N1 C2 1.488(4) .
N1 C1 1.494(4) .
N1 C1 1.494(4) 2_765
O1 C5 1.250(4) .
O2 C5 1.248(4) .
C5 C6 1.499(4) .
