#------------------------------------------------------------------------------
#$Date: 2017-09-19 09:31:49 +0300 (Tue, 19 Sep 2017) $
#$Revision: 201022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/92/7229206.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_7229206
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            'C4 H11 N O3'
_chemical_formula_weight         121.14
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.806(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6326(3)
_cell_length_b                   9.1273(3)
_cell_length_c                   9.7984(3)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.91
_cell_measurement_theta_min      2.76
_cell_volume                     659.94(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.981
_diffrn_reflns_theta_min         3.035
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0390
_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)+(0.0736P)²+0.0821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2463
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp05710e2.cif
_cod_data_source_block           NH3EtOH-OAc
_cod_database_code               7229206
_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   0.974
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.16745(9) 0.34666(7) 0.62546(6) 0.03201(14) Uani 1 1 d .
H1C H 0.1450(19) 0.3268(14) 0.5302(15) 0.048 Uiso 1 1 d U
O2 O 0.36031(8) 0.15305(7) 0.38873(5) 0.02907(13) Uani 1 1 d .
O3 O 0.10688(7) 0.28383(6) 0.34850(5) 0.02507(12) Uani 1 1 d .
N1 N 0.13024(7) 0.53883(6) 0.84548(6) 0.01934(11) Uani 1 1 d .
H1D H 0.1467(15) 0.5793(13) 0.9337(12) 0.029 Uiso 1 1 d U
H1E H 0.0559(15) 0.4598(13) 0.8430(12) 0.029 Uiso 1 1 d U
H1F H 0.0639(15) 0.6006(13) 0.7819(12) 0.029 Uiso 1 1 d U
C1 C 0.30604(9) 0.50169(8) 0.81534(8) 0.02581(14) Uani 1 1 d .
H1A H 0.3564(15) 0.4168(13) 0.8699(12) 0.031 Uiso 1 1 d U
H1B H 0.3852(15) 0.5823(12) 0.8442(12) 0.031 Uiso 1 1 d U
C2 C 0.28033(10) 0.47059(8) 0.66031(8) 0.02662(14) Uani 1 1 d .
H2A H 0.2238(16) 0.5591(12) 0.6029(12) 0.032 Uiso 1 1 d U
H2B H 0.4005(15) 0.4485(13) 0.6448(12) 0.032 Uiso 1 1 d U
C3 C 0.23797(8) 0.22836(7) 0.30985(6) 0.01887(12) Uani 1 1 d .
C4 C 0.24839(11) 0.25768(11) 0.16008(7) 0.03288(18) Uani 1 1 d .
H4A H 0.3554(19) 0.2076(17) 0.1440(14) 0.049 Uiso 1 1 d U
H4B H 0.1407(18) 0.2279(17) 0.0971(15) 0.049 Uiso 1 1 d U
H4C H 0.2626(18) 0.3727(17) 0.1476(15) 0.049 Uiso 1 1 d U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
N1 C1 C2 110.59(5)
O1 C2 C1 108.00(6)
O2 C3 O3 123.85(6)
O2 C3 C4 118.63(6)
O3 C3 C4 117.50(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4100(9)
O2 C3 1.2542(7)
O3 C3 1.2628(8)
N1 C1 1.4850(9)
C1 C2 1.5080(10)
C3 C4 1.5136(9)
