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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520239.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_1520239
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 4-Methylimidazolium hemisuccinate hemisuccinic acid
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              473
_journal_year                    2008
_chemical_formula_sum            'C8 H12 N2 O4'
_chemical_formula_weight         200.20
_chemical_name_systematic
;
Succinic acid & 4-methylimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.299(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9015(2)
_cell_length_b                   17.3293(10)
_cell_length_c                   13.8628(7)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     931.61(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9780
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0490
_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)+(0.0425P)²+0.4542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                1562
_reflns_number_total             2117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-473.cif
_cod_data_source_block           06skc0051p21c
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/473)

More at:
http://ecrystals.chem.soton.ac.uk/473/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520239
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2363(5) -0.03345(11) 0.88098(12) 0.0200(4) Uani 1 1 d . . .
C2 C 0.4277(5) 0.02003(11) 0.95350(12) 0.0210(4) Uani 1 1 d . . .
H2A H 0.2697 0.0616 0.9696 0.025 Uiso 1 1 calc R . .
H2B H 0.6198 0.0443 0.9235 0.025 Uiso 1 1 calc R . .
O1A O 0.1840(4) -0.10088(8) 0.89667(10) 0.0320(4) Uani 1 1 d . . .
O1B O 0.1261(4) 0.00217(8) 0.79940(9) 0.0280(3) Uani 1 1 d . . .
H1 H 0.0259 -0.0296 0.7602 0.058(8) Uiso 1 1 calc R . .
C22 C 0.3031(5) 0.25873(11) 0.67050(13) 0.0239(4) Uani 1 1 d . . .
H22 H 0.1675 0.2901 0.6248 0.029 Uiso 1 1 calc R . .
C24 C 0.6037(5) 0.21833(11) 0.80502(13) 0.0206(4) Uani 1 1 d . . .
C25 C 0.6007(5) 0.16166(11) 0.73784(13) 0.0227(4) Uani 1 1 d . . .
H25 H 0.7090 0.1127 0.7466 0.027 Uiso 1 1 calc R . .
C26 C 0.7673(5) 0.22233(12) 0.90688(13) 0.0257(4) Uani 1 1 d . . .
H26A H 0.5878 0.2233 0.9511 0.039 Uiso 1 1 calc R . .
H26B H 0.9072 0.2693 0.9158 0.039 Uiso 1 1 calc R . .
H26C H 0.9147 0.1770 0.9210 0.039 Uiso 1 1 calc R . .
N21 N 0.4121(4) 0.18790(9) 0.65438(11) 0.0230(4) Uani 1 1 d . . .
H21 H 0.3709 0.1620 0.5997 0.042(7) Uiso 1 1 calc R . .
N23 N 0.4144(4) 0.27849(9) 0.76064(11) 0.0213(4) Uani 1 1 d . . .
H23 H 0.3744 0.3229 0.7880 0.047(7) Uiso 1 1 calc R . .
C31 C 0.1884(5) 0.42356(10) 0.91659(12) 0.0183(4) Uani 1 1 d . . .
C32 C 0.0245(5) 0.49764(10) 0.94629(12) 0.0188(4) Uani 1 1 d . . .
H32B H -0.2033 0.5033 0.9078 0.023 Uiso 1 1 calc R . .
H32A H 0.1698 0.5415 0.9299 0.023 Uiso 1 1 calc R . .
O31B O 0.3141(3) 0.37607(7) 0.97756(9) 0.0249(3) Uani 1 1 d . . .
O31A O 0.1961(3) 0.41353(8) 0.82538(9) 0.0256(3) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1A C1 O1B 124.11(17) . .
O1A C1 C2 123.78(16) . .
O1B C1 C2 112.10(16) . .
C1 C2 C2 113.39(19) . 3_657
C1 C2 H2A 108.9 . .
C2 C2 H2A 108.9 3_657 .
C1 C2 H2B 108.9 . .
C2 C2 H2B 108.9 3_657 .
H2A C2 H2B 107.7 . .
C1 O1B H1 109.5 . .
N23 C22 N21 108.73(17) . .
N23 C22 H22 125.6 . .
N21 C22 H22 125.6 . .
C25 C24 N23 106.10(16) . .
C25 C24 C26 131.18(18) . .
N23 C24 C26 122.72(16) . .
C24 C25 N21 107.57(16) . .
C24 C25 H25 126.2 . .
N21 C25 H25 126.2 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C22 N21 C25 108.38(15) . .
C22 N21 H21 125.8 . .
C25 N21 H21 125.8 . .
C22 N23 C24 109.23(16) . .
C22 N23 H23 125.4 . .
C24 N23 H23 125.4 . .
O31B C31 O31A 122.16(16) . .
O31B C31 C32 121.67(15) . .
O31A C31 C32 116.16(15) . .
C31 C32 C32 114.44(19) . 3_567
C31 C32 H32B 108.6 . .
C32 C32 H32B 108.6 3_567 .
C31 C32 H32A 108.6 . .
C32 C32 H32A 108.6 3_567 .
H32B C32 H32A 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.210(2) .
C1 O1B 1.318(2) .
C1 C2 1.504(3) .
C2 C2 1.517(3) 3_657
C2 H2A 0.9900 .
C2 H2B 0.9900 .
O1B H1 0.8400 .
C22 N23 1.322(2) .
C22 N21 1.326(2) .
C22 H22 0.9500 .
C24 C25 1.353(3) .
C24 N23 1.382(2) .
C24 C26 1.486(3) .
C25 N21 1.379(2) .
C25 H25 0.9500 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
N21 H21 0.8800 .
N23 H23 0.8800 .
C31 O31B 1.241(2) .
C31 O31A 1.280(2) .
C31 C32 1.511(2) .
C32 C32 1.524(3) 3_567
C32 H32B 0.9900 .
C32 H32A 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N23 H23 O31A 0.88 1.82 2.679(2) 166.3 .
O1B H1 O31A 0.84 1.70 2.5406(18) 174.3 2_546
N21 H21 O31B 0.88 1.81 2.679(2) 169.9 4_565
