#------------------------------------------------------------------------------
#$Date: 2017-09-19 09:31:49 +0300 (Tue, 19 Sep 2017) $
#$Revision: 201022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/92/7229205.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_7229205
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            'C2 H7 N O3'
_chemical_formula_weight         93.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_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                 99.565(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3033(5)
_cell_length_b                   8.6135(6)
_cell_length_c                   6.8992(4)
_cell_measurement_reflns_used    3507
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.83
_cell_volume                     427.97(5)
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_min         2.828
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0302
_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)+(0.0536P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                956
_reflns_number_total             1067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp05710e2.cif
_cod_data_source_block           NH3OH-OAc
_cod_database_code               7229205
_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_res_file
; 
  
    p1.res created by SHELXL-2014/7 
  
  
TITL p1 in P2(1)/c 
CELL 0.71073   7.30330   8.61350   6.89920  90.0000  99.5646  90.0000 
ZERR    4.00   0.00050   0.00060   0.00040   0.0000   0.0031   0.0000 
LATT  1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 8 28 4 12 
  
L.S. 10 
ACTA 
FMAP 2 
PLAN 5 
TEMP 23.000 
  
WGHT    0.053600    0.139800 
FVAR       0.39709 
O1    4    0.959116    0.292068    0.178441    11.00000    0.01346    0.01761 = 
         0.02248    0.00087   -0.00167   -0.00058 
O2    4    0.677730    0.349100    0.023421    11.00000    0.01460    0.01322 = 
         0.02508   -0.00053   -0.00298    0.00102 
O3    4    0.369970    0.288665   -0.185936    11.00000    0.01224    0.02124 = 
         0.01921   -0.00474    0.00098    0.00026 
H3    2    0.488373    0.308953   -0.108054    11.00000   -1.50000 
N2    3    0.238168    0.343272   -0.071567    11.00000    0.01368    0.01401 = 
         0.01696   -0.00044    0.00181   -0.00014 
H2A   2    0.257372    0.300547    0.045443    11.00000   -1.50000 
H2B   2    0.250675    0.450193   -0.057356    11.00000   -1.50000 
H2C   2    0.125986    0.314750   -0.139108    11.00000   -1.50000 
C1    1    0.755687    0.080554    0.065435    11.00000    0.02101    0.01283 = 
         0.02478   -0.00031    0.00128   -0.00044 
H1A   2    0.853932    0.015677    0.127347    11.00000   -1.50000 
H1B   2    0.729896    0.056953   -0.066117    11.00000   -1.50000 
H1C   2    0.648219    0.057953    0.117527    11.00000   -1.50000 
C2    1    0.803124    0.250538    0.092494    11.00000    0.01341    0.01389 = 
         0.01522    0.00008    0.00213    0.00051 
HKLF 4 
  
REM  p1 in P2(1)/c 
REM R1 =  0.0302 for     956 Fo > 4sig(Fo)  and  0.0338 for all    1067 data 
REM     76 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0503      0.0947 
  
REM Highest difference peak  0.194,  deepest hole -0.241,  1-sigma level  0.052 
Q1    1   0.5744  0.3170 -0.0005  11.00000  0.05    0.19 
Q2    1   1.0228  0.3417  0.1017  11.00000  0.05    0.17 
Q3    1   0.8367  0.0424 -0.0393  11.00000  0.05    0.16 
Q4    1   0.8816  0.2604  0.2216  11.00000  0.05    0.16 
Q5    1   0.7806  0.1642  0.0919  11.00000  0.05    0.16 
;
_shelx_res_checksum              99006
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-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_adp
O1 O 0.95912(9) 0.29207(8) 0.17844(11) 0.01838(19) Uani 1 1 d .
O2 O 0.67773(9) 0.34910(8) 0.02342(11) 0.01835(19) Uani 1 1 d .
O3 O 0.36997(9) 0.28866(8) -0.18594(10) 0.01775(19) Uani 1 1 d .
H3 H 0.488(2) 0.3090(16) -0.108(2) 0.027 Uiso 1 1 d U
N2 N 0.23817(11) 0.34327(9) -0.07157(12) 0.0150(2) Uani 1 1 d .
H2A H 0.257(2) 0.3005(16) 0.045(2) 0.022 Uiso 1 1 d U
H2B H 0.2507(18) 0.4502(17) -0.0574(19) 0.022 Uiso 1 1 d U
H2C H 0.126(2) 0.3147(16) -0.139(2) 0.022 Uiso 1 1 d U
C1 C 0.75569(14) 0.08055(11) 0.06544(16) 0.0198(2) Uani 1 1 d .
H1A H 0.854(2) 0.0157(18) 0.127(2) 0.030 Uiso 1 1 d U
H1B H 0.730(2) 0.0570(17) -0.066(2) 0.030 Uiso 1 1 d U
H1C H 0.6482(19) 0.0580(18) 0.118(2) 0.030 Uiso 1 1 d U
C2 C 0.80312(12) 0.25054(11) 0.09249(13) 0.0142(2) 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
O1 0.0135(3) 0.0176(4) 0.0225(4) 0.0009(3) -0.0017(3) -0.0006(2)
O2 0.0146(3) 0.0132(3) 0.0251(4) -0.0005(2) -0.0030(3) 0.0010(2)
O3 0.0122(3) 0.0212(4) 0.0192(4) -0.0047(3) 0.0010(3) 0.0003(2)
N2 0.0137(4) 0.0140(4) 0.0170(4) -0.0004(3) 0.0018(3) -0.0001(3)
C1 0.0210(5) 0.0128(4) 0.0248(5) -0.0003(3) 0.0013(4) -0.0004(3)
C2 0.0134(4) 0.0139(4) 0.0152(4) 0.0001(3) 0.0021(3) 0.0005(3)
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
O1 C2 O2 121.82(9)
O1 C2 C1 120.69(8)
O2 C2 C1 117.50(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2462(11)
O2 C2 1.2812(11)
O3 N2 1.4223(10)
C1 C2 1.5090(13)
