#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/20/2232082.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232082
loop_
_publ_author_name
'Zhu, Run-Qiang'
'Yu, Chun-Hua'
_publ_section_title
;
 2-Ethylimidazolium terephthalate
;
_journal_coeditor_code           VM2120
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2746
_journal_paper_doi               10.1107/S1600536811038578
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          ' C5 H9 N2 +, C8 H5 O4 -'
_chemical_formula_moiety         ' C5 H9 N2, C8 H5 O4'
_chemical_formula_sum            'C13 H14 N2 O4'
_chemical_formula_weight         262.26
_chemical_name_systematic
;
 2-Ethylimidazolium terephthalate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.60(3)
_cell_angle_beta                 78.77(3)
_cell_angle_gamma                89.50(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4587(13)
_cell_length_b                   7.0719(14)
_cell_length_c                   14.688(3)
_cell_measurement_reflns_used    2933
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      2.2
_cell_volume                     644.7(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'CCD Profile fitting scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6568
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.240
_refine_ls_extinction_coef       0.084(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.3515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                2197
_reflns_number_total             2933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            vm2120.cif
_cod_data_source_block           I
_cod_database_code               2232082
_cod_database_fobs_code          2232082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7347(7) 0.9795(9) 0.2520(3) 0.0599(13) Uani d P 0.808(14) 1 A 1
H H1A 0.6126 1.0576 0.2508 0.090 Uiso calc PR 0.808(14) 1 A 1
H H1B 0.8455 1.0340 0.1999 0.090 Uiso calc PR 0.808(14) 1 A 1
H H1C 0.7815 0.9756 0.3105 0.090 Uiso calc PR 0.808(14) 1 A 1
C C2 0.6784(7) 0.7753(6) 0.2440(3) 0.0508(13) Uani d P 0.808(14) 1 A 1
H H2A 0.5645 0.7218 0.2961 0.061 Uiso calc PR 0.808(14) 1 A 1
H H2B 0.6286 0.7802 0.1854 0.061 Uiso calc PR 0.808(14) 1 A 1
C C1' 0.544(5) 0.812(5) 0.2476(14) 0.113(11) Uani d P 0.192(14) 1 A 2
H H1'A 0.4549 0.9202 0.2539 0.170 Uiso calc PR 0.192(14) 1 A 2
H H1'B 0.4893 0.7036 0.2965 0.170 Uiso calc PR 0.192(14) 1 A 2
H H1'C 0.5486 0.7805 0.1867 0.170 Uiso calc PR 0.192(14) 1 A 2
C C2' 0.759(4) 0.863(4) 0.2564(12) 0.068(7) Uani d P 0.192(14) 1 A 2
H H2'A 0.7635 0.8948 0.3174 0.082 Uiso calc PR 0.192(14) 1 A 2
H H2'B 0.8256 0.9671 0.2057 0.082 Uiso calc PR 0.192(14) 1 A 2
C C3 0.8617(4) 0.6470(4) 0.24548(17) 0.0477(6) Uani d . 1 1 . .
C C4 1.1731(4) 0.5205(4) 0.21494(18) 0.0477(6) Uani d . 1 1 . .
H H4 1.3152 0.5068 0.1905 0.057 Uiso calc R 1 1 A .
C C5 1.0399(4) 0.3850(4) 0.27270(18) 0.0511(6) Uani d . 1 1 A .
H H5 1.0717 0.2583 0.2960 0.061 Uiso calc R 1 1 . .
C C6 0.3529(3) 0.2725(3) 0.46010(16) 0.0378(5) Uani d . 1 1 . .
C C7 0.1695(3) 0.1309(3) 0.48246(14) 0.0327(5) Uani d . 1 1 . .
C C8 0.1917(3) -0.0380(3) 0.44744(16) 0.0392(5) Uani d . 1 1 . .
H H8 0.3206 -0.0636 0.4118 0.047 Uiso calc R 1 1 . .
C C9 0.0230(4) -0.1691(3) 0.46529(16) 0.0398(5) Uani d . 1 1 . .
H H9 0.0394 -0.2826 0.4421 0.048 Uiso calc R 1 1 . .
C C10 0.2463(3) 0.1473(3) 1.03616(15) 0.0356(5) Uani d . 1 1 . .
C C11 0.3795(3) 0.3302(3) 1.01537(14) 0.0303(5) Uani d . 1 1 . .
C C12 0.3127(3) 0.5022(3) 0.96744(15) 0.0336(5) Uani d . 1 1 . .
H H12 0.1871 0.5039 0.9453 0.040 Uiso calc R 1 1 . .
C C13 0.4326(3) 0.6717(3) 0.95247(15) 0.0336(5) Uani d . 1 1 . .
H H13 0.3867 0.7866 0.9208 0.040 Uiso calc R 1 1 . .
N N1 0.8498(3) 0.4672(3) 0.29095(14) 0.0505(6) Uani d . 1 1 A .
H H1D 0.7379 0.4096 0.3271 0.061 Uiso calc R 1 1 . .
N N2 1.0596(3) 0.6826(3) 0.19901(14) 0.0472(5) Uani d . 1 1 A .
H H2C 1.1087 0.7915 0.1642 0.057 Uiso calc R 1 1 . .
O O1 0.2779(3) 0.0121(2) 1.09758(13) 0.0556(5) Uani d . 1 1 . .
O O2 0.1042(3) 0.1504(2) 0.98639(14) 0.0573(5) Uani d . 1 1 . .
H H2 0.0476 0.0429 0.9968 0.086 Uiso calc PR 0.50 1 . .
O O3 0.4954(3) 0.2675(3) 0.39276(13) 0.0595(6) Uani d . 1 1 . .
O O4 0.3451(3) 0.3907(3) 0.51614(14) 0.0648(6) Uani d . 1 1 . .
H H4A 0.4374 0.4752 0.4941 0.097 Uiso calc PR 0.50 1 . .
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_site_symmetry_1
_geom_angle
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C3 C2 C1 . 112.1(4)
C3 C2 H2A . 109.2
C1 C2 H2A . 109.2
C3 C2 H2B . 109.2
C1 C2 H2B . 109.2
H2A C2 H2B . 107.9
C2' C1' H1'A . 109.5
C2' C1' H1'B . 109.5
H1'A C1' H1'B . 109.5
C2' C1' H1'C . 109.5
H1'A C1' H1'C . 109.5
H1'B C1' H1'C . 109.5
C1' C2' C3 . 96(2)
C1' C2' H2'A . 112.6
C3 C2' H2'A . 112.6
C1' C2' H2'B . 112.6
C3 C2' H2'B . 112.6
H2'A C2' H2'B . 110.1
N1 C3 N2 . 107.0(2)
N1 C3 C2 . 124.2(3)
N2 C3 C2 . 128.7(2)
N1 C3 C2' . 140.7(6)
N2 C3 C2' . 106.2(7)
C2 C3 C2' . 31.6(7)
C5 C4 N2 . 106.4(2)
C5 C4 H4 . 126.8
N2 C4 H4 . 126.8
C4 C5 N1 . 107.0(2)
C4 C5 H5 . 126.5
N1 C5 H5 . 126.5
O3 C6 O4 . 125.1(2)
O3 C6 C7 . 119.7(2)
O4 C6 C7 . 115.20(19)
C9 C7 C8 2_556 119.54(18)
C9 C7 C6 2_556 121.07(19)
C8 C7 C6 . 119.35(19)
C7 C8 C9 . 120.4(2)
C7 C8 H8 . 119.8
C9 C8 H8 . 119.8
C7 C9 C8 2_556 120.0(2)
C7 C9 H9 2_556 120.0
C8 C9 H9 . 120.0
O1 C10 O2 . 125.55(19)
O1 C10 C11 . 119.7(2)
O2 C10 C11 . 114.72(19)
C13 C11 C12 2_667 119.61(18)
C13 C11 C10 2_667 119.44(18)
C12 C11 C10 . 120.91(18)
C13 C12 C11 . 120.29(19)
C13 C12 H12 . 119.9
C11 C12 H12 . 119.9
C11 C13 C12 2_667 120.10(19)
C11 C13 H13 2_667 120.0
C12 C13 H13 . 120.0
C3 N1 C5 . 110.0(2)
C3 N1 H1D . 125.0
C5 N1 H1D . 125.0
C3 N2 C4 . 109.5(2)
C3 N2 H2C . 125.2
C4 N2 H2C . 125.2
C10 O2 H2 . 109.5
C6 O4 H4A . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.525(7)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 C3 . 1.486(5)
C2 H2A . 0.9700
C2 H2B . 0.9700
C1' C2' . 1.47(4)
C1' H1'A . 0.9600
C1' H1'B . 0.9600
C1' H1'C . 0.9600
C2' C3 . 1.69(3)
C2' H2'A . 0.9700
C2' H2'B . 0.9700
C3 N1 . 1.310(3)
C3 N2 . 1.327(3)
C4 C5 . 1.337(3)
C4 N2 . 1.361(3)
C4 H4 . 0.9300
C5 N1 . 1.356(4)
C5 H5 . 0.9300
C6 O3 . 1.219(3)
C6 O4 . 1.278(3)
C6 C7 . 1.501(3)
C7 C9 2_556 1.383(3)
C7 C8 . 1.387(3)
C8 C9 . 1.388(3)
C8 H8 . 0.9300
C9 C7 2_556 1.383(3)
C9 H9 . 0.9300
C10 O1 . 1.224(3)
C10 O2 . 1.277(3)
C10 C11 . 1.506(3)
C11 C13 2_667 1.384(3)
C11 C12 . 1.390(3)
C12 C13 . 1.389(3)
C12 H12 . 0.9300
C13 C11 2_667 1.384(3)
C13 H13 . 0.9300
N1 H1D . 0.8600
N2 H2C . 0.8600
O2 H2 . 0.8200
O4 H4A . 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4A O4 2_666 0.82 1.67 2.452(3) 159.5
O2 H2 O2 2_557 0.82 1.64 2.450(3) 169.5
N2 H2C O1 1_664 0.86 1.90 2.739(3) 166.1
N1 H1D O3 . 0.86 1.86 2.713(3) 172.6
