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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/1/51/99/1519994.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_1519994
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 1,2-Dimethylimidazolium fumarate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              512
_journal_year                    2008
_chemical_formula_sum            'C9 H12 N2 O4'
_chemical_formula_weight         212.21
_chemical_name_systematic
;
Fumaric acid and 1,2-dimethylimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.547(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6480(7)
_cell_length_b                   11.6730(9)
_cell_length_c                   11.2040(11)
_cell_measurement_reflns_used    4271
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     998.32(15)
_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  0.1219
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15218
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.9911
_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    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1724
_refine_ls_R_factor_gt           0.1020
_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)+(0.0000P)²+3.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                1382
_reflns_number_total             2279
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-512.cif
_cod_data_source_block           07skc0022p21n
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/512)

More at:
http://ecrystals.chem.soton.ac.uk/512/
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1519994
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0819(5) 0.0450(3) -0.6566(4) 0.0241(9) Uani 1 1 d . . .
C2 C 0.1223(6) 0.1612(4) -0.6052(4) 0.0252(10) Uani 1 1 d . . .
H2 H 0.0666 0.2264 -0.6413 0.030 Uiso 1 1 calc R . .
C3 C 0.2326(6) 0.1756(3) -0.5114(4) 0.0253(10) Uani 1 1 d . . .
H3 H 0.2879 0.1097 -0.4766 0.030 Uiso 1 1 calc R . .
C4 C 0.2755(5) 0.2888(4) -0.4570(4) 0.0230(9) Uani 1 1 d . . .
O1A O 0.1597(4) -0.0407(2) -0.6097(2) 0.0259(7) Uani 1 1 d . . .
O1B O -0.0275(4) 0.0390(2) -0.7462(3) 0.0286(7) Uani 1 1 d . . .
O4A O 0.3851(4) 0.2795(2) -0.3606(3) 0.0291(8) Uani 1 1 d . . .
H4 H 0.4099 0.3451 -0.3338 0.07(2) Uiso 1 1 calc R . .
O4B O 0.2158(4) 0.3796(2) -0.4949(3) 0.0317(8) Uani 1 1 d . . .
C22 C 0.4288(5) 0.1716(3) -0.8042(4) 0.0232(9) Uani 1 1 d . . .
C24 C 0.5684(5) 0.2749(4) -0.6652(4) 0.0249(10) Uani 1 1 d . . .
H24 H 0.6098 0.3390 -0.6196 0.030 Uiso 1 1 calc R . .
C25 C 0.6086(6) 0.1650(4) -0.6425(4) 0.0251(10) Uani 1 1 d . . .
H25 H 0.6823 0.1365 -0.5779 0.030 Uiso 1 1 calc R . .
C26 C 0.5307(6) -0.0242(3) -0.7456(4) 0.0269(10) Uani 1 1 d . . .
H26A H 0.4721 -0.0463 -0.8224 0.040 Uiso 1 1 calc R . .
H26B H 0.4726 -0.0614 -0.6804 0.040 Uiso 1 1 calc R . .
H26C H 0.6537 -0.0481 -0.7435 0.040 Uiso 1 1 calc R . .
C27 C 0.3165(6) 0.1413(4) -0.9120(4) 0.0269(10) Uani 1 1 d . . .
H27A H 0.3904 0.1184 -0.9763 0.040 Uiso 1 1 calc R . .
H27B H 0.2456 0.2078 -0.9378 0.040 Uiso 1 1 calc R . .
H27C H 0.2393 0.0776 -0.8933 0.040 Uiso 1 1 calc R . .
N21 N 0.5215(5) 0.1011(3) -0.7316(3) 0.0249(8) Uani 1 1 d . . .
N23 N 0.4573(4) 0.2785(3) -0.7658(3) 0.0240(8) Uani 1 1 d . . .
H23 H 0.4122 0.3409 -0.7994 0.030(13) 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(4) . .
O1A C1 C2 118.5(4) . .
O1B C1 C2 117.7(4) . .
C3 C2 C1 121.9(4) . .
C3 C2 H2 119.0 . .
C1 C2 H2 119.0 . .
C2 C3 C4 123.8(4) . .
C2 C3 H3 118.1 . .
C4 C3 H3 118.1 . .
O4B C4 O4A 123.8(4) . .
O4B C4 C3 124.2(4) . .
O4A C4 C3 112.0(4) . .
C4 O4A H4 109.5 . .
N21 C22 N23 108.1(4) . .
N21 C22 C27 127.7(4) . .
N23 C22 C27 124.2(4) . .
C25 C24 N23 108.0(4) . .
C25 C24 H24 126.0 . .
N23 C24 H24 126.0 . .
C24 C25 N21 106.5(4) . .
C24 C25 H25 126.7 . .
N21 C25 H25 126.7 . .
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 108.8(3) . .
C22 N21 C26 125.2(4) . .
C25 N21 C26 126.0(4) . .
C22 N23 C24 108.5(4) . .
C22 N23 H23 125.8 . .
C24 N23 H23 125.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.262(5) .
C1 O1B 1.268(5) .
C1 C2 1.498(6) .
C2 C3 1.317(6) .
C2 H2 0.9500 .
C3 C4 1.483(6) .
C3 H3 0.9500 .
C4 O4B 1.220(5) .
C4 O4A 1.330(5) .
O4A H4 0.8400 .
C22 N21 1.331(5) .
C22 N23 1.333(5) .
C22 C27 1.481(6) .
C24 C25 1.340(6) .
C24 N23 1.370(5) .
C24 H24 0.9500 .
C25 N21 1.383(5) .
C25 H25 0.9500 .
C26 N21 1.473(5) .
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
O4A H4 O1B 0.84 1.72 2.544(4) 165.6 4_666
N23 H23 O1A 0.88 1.78 2.655(4) 169.8 2_553
N23 H23 O1B 0.88 2.52 3.090(4) 123.4 2_553
