#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520209.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_1520209
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 1,2-Dimethylimidazolium succinate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              461
_journal_year                    2008
_chemical_formula_sum            'C9 H14 N2 O4'
_chemical_formula_weight         214.22
_chemical_name_systematic
;
Succinic acid & 1,2-dimethylimidazole
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.5769(12)
_cell_length_b                   7.3521(4)
_cell_length_c                   14.0383(8)
_cell_measurement_reflns_used    8890
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2123.8(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1637
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43931
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9916
_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    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.7769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1643
_reflns_number_total             2444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-461.cif
_cod_data_source_block           06skc0028pccn
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/461)

More at:
http://ecrystals.chem.soton.ac.uk/461/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      Pccn
_cod_database_code               1520209
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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 0.56211(12) 0.2711(4) 0.66607(18) 0.0288(6) Uani 1 1 d . . .
C2 C 0.51884(12) 0.1712(4) 0.73457(18) 0.0311(6) Uani 1 1 d . . .
H2A H 0.5187 0.0407 0.7173 0.037 Uiso 1 1 calc R . .
H2B H 0.4739 0.2171 0.7270 0.037 Uiso 1 1 calc R . .
C3 C 0.53814(13) 0.1886(4) 0.83846(18) 0.0300(6) Uani 1 1 d . . .
H3A H 0.5427 0.3194 0.8539 0.036 Uiso 1 1 calc R . .
H3B H 0.5024 0.1396 0.8782 0.036 Uiso 1 1 calc R . .
C4 C 0.60058(12) 0.0926(4) 0.86581(19) 0.0291(6) Uani 1 1 d . . .
O1A O 0.60443(9) 0.3772(3) 0.68932(13) 0.0378(5) Uani 1 1 d . . .
O1B O 0.54796(9) 0.2313(3) 0.57668(13) 0.0349(5) Uani 1 1 d . . .
H1 H 0.5757 0.2786 0.5405 0.068(12) Uiso 1 1 calc R . .
O4A O 0.62345(9) 0.1348(3) 0.94797(12) 0.0361(5) Uani 1 1 d . . .
O4B O 0.62504(9) -0.0219(3) 0.81241(13) 0.0364(5) Uani 1 1 d . . .
C22 C 0.71067(13) 0.5402(4) 0.95590(19) 0.0339(6) Uani 1 1 d . . .
C24 C 0.74885(15) 0.4887(4) 1.10051(19) 0.0364(7) Uani 1 1 d . . .
H24 H 0.7774 0.4546 1.1506 0.044 Uiso 1 1 calc R . .
C25 C 0.68822(14) 0.5515(4) 1.1099(2) 0.0383(7) Uani 1 1 d . . .
H25 H 0.6655 0.5701 1.1680 0.046 Uiso 1 1 calc R . .
C26 C 0.60115(13) 0.6610(4) 0.9977(2) 0.0481(8) Uani 1 1 d . . .
H26A H 0.5964 0.6762 0.9287 0.072 Uiso 1 1 calc R . .
H26B H 0.5970 0.7796 1.0290 0.072 Uiso 1 1 calc R . .
H26C H 0.5673 0.5789 1.0213 0.072 Uiso 1 1 calc R . .
C27 C 0.70486(15) 0.5477(4) 0.85174(19) 0.0430(7) Uani 1 1 d . . .
H27A H 0.6749 0.4529 0.8301 0.064 Uiso 1 1 calc R . .
H27B H 0.7477 0.5282 0.8229 0.064 Uiso 1 1 calc R . .
H27C H 0.6882 0.6672 0.8328 0.064 Uiso 1 1 calc R . .
N21 N 0.66477(10) 0.5844(3) 1.01855(16) 0.0326(5) Uani 1 1 d . . .
N23 N 0.76225(11) 0.4826(3) 1.00354(16) 0.0336(5) Uani 1 1 d . . .
H23 H 0.7991 0.4463 0.9779 0.071(12) Uiso 1 1 calc R . .
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 123.8(2) . .
O1A C1 C2 124.6(2) . .
O1B C1 C2 111.7(2) . .
C1 C2 C3 114.8(2) . .
C1 C2 H2A 108.6 . .
C3 C2 H2A 108.6 . .
C1 C2 H2B 108.6 . .
C3 C2 H2B 108.6 . .
H2A C2 H2B 107.6 . .
C4 C3 C2 115.2(2) . .
C4 C3 H3A 108.5 . .
C2 C3 H3A 108.5 . .
C4 C3 H3B 108.5 . .
C2 C3 H3B 108.5 . .
H3A C3 H3B 107.5 . .
O4B C4 O4A 124.1(2) . .
O4B C4 C3 120.6(2) . .
O4A C4 C3 115.2(2) . .
C1 O1B H1 109.5 . .
N23 C22 N21 108.3(2) . .
N23 C22 C27 125.5(3) . .
N21 C22 C27 126.2(3) . .
C25 C24 N23 107.1(2) . .
C25 C24 H24 126.5 . .
N23 C24 H24 126.5 . .
C24 C25 N21 107.0(2) . .
C24 C25 H25 126.5 . .
N21 C25 H25 126.5 . .
N21 C26 H26A 109.5 . .
N21 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
N21 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C22 C27 H27A 109.5 . .
C22 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C22 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C22 N21 C25 108.7(2) . .
C22 N21 C26 126.9(2) . .
C25 N21 C26 124.4(2) . .
C22 N23 C24 109.0(2) . .
C22 N23 H23 125.5 . .
C24 N23 H23 125.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.214(3) .
C1 O1B 1.321(3) .
C1 C2 1.502(4) .
C2 C3 1.517(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.516(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 O4B 1.234(3) .
C4 O4A 1.284(3) .
O1B H1 0.8400 .
C22 N23 1.324(3) .
C22 N21 1.331(3) .
C22 C27 1.468(4) .
C24 C25 1.337(4) .
C24 N23 1.390(3) .
C24 H24 0.9500 .
C25 N21 1.392(4) .
C25 H25 0.9500 .
C26 N21 1.455(3) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
N23 H23 0.8800 .
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
O1B H1 O4A 0.84 1.75 2.578(3) 169.2 7_565
N23 H23 O4A 0.88 1.75 2.624(3) 169.7 2_655
