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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/1/51/99/1519997.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_1519997
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 2-Methylimidazolium hemiadipate hemiadipic acid hydrate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              521
_journal_year                    2008
_chemical_formula_sum            'C10 H18 N2 O5'
_chemical_formula_weight         246.26
_chemical_name_systematic
;
Adipic Acid and 2-Methylimidazole
;
_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
_cell_angle_alpha                96.9510(10)
_cell_angle_beta                 94.4750(10)
_cell_angle_gamma                107.3840(10)
_cell_formula_units_Z            2
_cell_length_a                   4.8629(3)
_cell_length_b                   7.9978(5)
_cell_length_c                   16.5263(11)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      2.96
_cell_volume                     604.44(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.67100
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5294
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9914
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0943P)²+0.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                2332
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-521.cif
_cod_data_source_block           ssf1337
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/521)

More at:
http://ecrystals.chem.soton.ac.uk/521/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.7807(3) 0.40566(17) 0.33759(8) 0.0163(3) Uani 1 1 d . . .
C2 C 0.6429(3) 0.51297(18) 0.39389(8) 0.0185(3) Uani 1 1 d . . .
H2A H 0.4645 0.5201 0.3633 0.022 Uiso 1 1 calc R . .
H2B H 0.7785 0.6351 0.4084 0.022 Uiso 1 1 calc R . .
C3 C 0.5643(3) 0.44049(17) 0.47294(8) 0.0171(3) Uani 1 1 d . . .
H3A H 0.7404 0.4306 0.5037 0.021 Uiso 1 1 calc R . .
H3B H 0.4220 0.3202 0.4593 0.021 Uiso 1 1 calc R . .
O1A O 0.8634(2) 0.28436(13) 0.36148(6) 0.0204(3) Uani 1 1 d . . .
O1B O 0.8110(2) 0.44534(14) 0.26538(6) 0.0236(3) Uani 1 1 d . . .
C22 C 0.7541(3) 0.98177(18) -0.23851(8) 0.0190(3) Uani 1 1 d . . .
C24 C 0.8726(3) 0.79678(19) -0.16389(9) 0.0224(3) Uani 1 1 d . . .
H24 H 0.9491 0.7078 -0.1480 0.027 Uiso 1 1 calc R . .
C25 C 0.7328(3) 0.88782(18) -0.11766(9) 0.0211(3) Uani 1 1 d . . .
H25 H 0.6922 0.8757 -0.0630 0.025 Uiso 1 1 calc R . .
C26 C 0.7221(3) 1.0795(2) -0.30716(9) 0.0264(3) Uani 1 1 d . . .
H26A H 0.8656 1.0714 -0.3447 0.040 Uiso 1 1 calc R . .
H26B H 0.7533 1.2042 -0.2855 0.040 Uiso 1 1 calc R . .
H26C H 0.5264 1.0278 -0.3368 0.040 Uiso 1 1 calc R . .
N21 N 0.6602(3) 1.00224(15) -0.16544(7) 0.0191(3) Uani 1 1 d . . .
H21 H 0.5665 1.0770 -0.1500 0.041(6) Uiso 1 1 calc R . .
N23 N 0.8838(3) 0.85707(16) -0.23861(7) 0.0206(3) Uani 1 1 d . . .
H23 H 0.9641 0.8190 -0.2799 0.065(8) Uiso 1 1 calc R . .
C31 C 0.6964(3) 0.68076(17) 0.13572(8) 0.0153(3) Uani 1 1 d . . .
C32 C 0.8588(3) 0.55865(17) 0.10178(7) 0.0152(3) Uani 1 1 d . . .
H32A H 0.7406 0.4350 0.1037 0.018 Uiso 1 1 calc R . .
H32B H 1.0416 0.5832 0.1385 0.018 Uiso 1 1 calc R . .
C33 C 0.9331(3) 0.57167(17) 0.01500(8) 0.0153(3) Uani 1 1 d . . .
H33A H 1.0719 0.6901 0.0133 0.018 Uiso 1 1 calc R . .
H33B H 0.7550 0.5581 -0.0220 0.018 Uiso 1 1 calc R . .
O31A O 0.6259(2) 0.66787(14) 0.20949(6) 0.0218(3) Uani 1 1 d . . .
H31 H 0.6982 0.5969 0.2298 0.086(10) Uiso 1 1 calc R . .
O31B O 0.6304(2) 0.78562(13) 0.09504(6) 0.0189(3) Uani 1 1 d . . .
O1W O 0.7898(3) 0.0793(2) 0.49130(8) 0.0402(4) Uani 1 1 d D . .
H1W H 0.825(11) -0.010(4) 0.473(3) 0.19(2) Uiso 1 1 d D . .
H2W H 0.809(5) 0.151(3) 0.4574(13) 0.048(6) Uiso 1 1 d 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 121.60(12) . .
O1A C1 C2 120.90(11) . .
O1B C1 C2 117.50(12) . .
C1 C2 C3 115.17(11) . .
C1 C2 H2A 108.5 . .
C3 C2 H2A 108.5 . .
C1 C2 H2B 108.5 . .
C3 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
C2 C3 C3 111.66(13) . 2_666
C2 C3 H3A 109.3 . .
C3 C3 H3A 109.3 2_666 .
C2 C3 H3B 109.3 . .
C3 C3 H3B 109.3 2_666 .
H3A C3 H3B 107.9 . .
N23 C22 N21 107.53(12) . .
N23 C22 C26 125.85(13) . .
N21 C22 C26 126.62(13) . .
C25 C24 N23 107.14(13) . .
C25 C24 H24 126.4 . .
N23 C24 H24 126.4 . .
C24 C25 N21 106.51(12) . .
C24 C25 H25 126.7 . .
N21 C25 H25 126.7 . .
C22 C26 H26A 109.5 . .
C22 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C22 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C22 N21 C25 109.46(12) . .
C22 N21 H21 125.3 . .
C25 N21 H21 125.3 . .
C22 N23 C24 109.36(12) . .
C22 N23 H23 125.3 . .
C24 N23 H23 125.3 . .
O31B C31 O31A 121.60(12) . .
O31B C31 C32 121.74(11) . .
O31A C31 C32 116.66(11) . .
C31 C32 C33 116.18(10) . .
C31 C32 H32A 108.2 . .
C33 C32 H32A 108.2 . .
C31 C32 H32B 108.2 . .
C33 C32 H32B 108.2 . .
H32A C32 H32B 107.4 . .
C32 C33 C33 110.84(13) . 2_765
C32 C33 H33A 109.5 . .
C33 C33 H33A 109.5 2_765 .
C32 C33 H33B 109.5 . .
C33 C33 H33B 109.5 2_765 .
H33A C33 H33B 108.1 . .
C31 O31A H31 109.5 . .
H1W O1W H2W 111(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.2491(16) .
C1 O1B 1.2797(16) .
C1 C2 1.5162(18) .
C2 C3 1.5224(17) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C3 1.528(2) 2_666
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C22 N23 1.3297(17) .
C22 N21 1.3328(18) .
C22 C26 1.477(2) .
C24 C25 1.349(2) .
C24 N23 1.3781(19) .
C24 H24 0.9500 .
C25 N21 1.3820(18) .
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 1.2337(16) .
C31 O31A 1.2994(15) .
C31 C32 1.5132(17) .
C32 C33 1.5142(17) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.530(2) 2_765
C33 H33A 0.9900 .
C33 H33B 0.9900 .
O31A H31 0.8400 .
O1W H1W 0.814(18) .
O1W H2W 0.839(15) .
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
O31A H31 O1B 0.84 1.62 2.4609(14) 174.8 .
O1W H2W O1A 0.839(15) 2.008(16) 2.8357(16) 169(2) .
N21 H21 O31B 0.88 1.86 2.7277(15) 167.0 2_675
N23 H23 O1A 0.88 1.88 2.7529(15) 173.3 2_765
O1W H1W O1W 0.814(18) 2.16(4) 2.723(3) 126(4) 2_756
