#------------------------------------------------------------------------------
#$Date: 2022-03-29 10:56:01 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274070 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104916.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_8104916
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              181
_journal_page_last               183
_journal_paper_doi               10.1515/ncrs-2020-0507
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C5 H8 N2, H2 O'
_chemical_formula_sum            'C5 H10 N2 O'
_chemical_formula_weight         114.15
_chemical_name_common            '2,4-dimethylimidazole hydrate'
_chemical_name_systematic        '2,4-dimethylimidazole hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.349(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7212(4)
_cell_length_b                   11.1424(8)
_cell_length_c                   12.8211(9)
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.42
_cell_volume                     672.52(9)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3023
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         2.425
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.0383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                1557
_reflns_number_total             1582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0507_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               8104916
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5153(2) 0.71437(11) 0.51093(10) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.5133(2) 0.81707(12) 0.65708(10) 0.0393(3) Uani 1 1 d . . . . .
H2A H 0.472(5) 0.839(2) 0.717(2) 0.059(7) Uiso 1 1 d . . . . .
C1 C 0.4111(3) 0.71980(12) 0.60389(11) 0.0360(3) Uani 1 1 d . . . . .
C2 C 0.6901(3) 0.87642(13) 0.59414(13) 0.0422(3) Uani 1 1 d . . . . .
H2 H 0.792360 0.948236 0.610629 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6908(3) 0.81291(14) 0.50409(11) 0.0381(3) Uani 1 1 d . . . . .
C4 C 0.2098(4) 0.63294(15) 0.64498(14) 0.0482(4) Uani 1 1 d . . . . .
H4A H 0.056739 0.676547 0.676052 0.072 Uiso 1 1 calc R U . . .
H4B H 0.310313 0.582509 0.698370 0.072 Uiso 1 1 calc R U . . .
H4C H 0.129063 0.582293 0.587710 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8447(4) 0.8372(2) 0.40854(15) 0.0543(4) Uani 1 1 d . . . . .
H5A H 0.706676 0.851559 0.348855 0.081 Uiso 1 1 calc R U . . .
H5B H 0.962909 0.767831 0.393875 0.081 Uiso 1 1 calc R U . . .
H5C H 0.965501 0.908214 0.420304 0.081 Uiso 1 1 calc R U . . .
O1 O 0.4029(2) 0.56654(9) 0.34354(8) 0.0373(3) Uani 1 1 d . . . . .
H1A H 0.246(6) 0.530(2) 0.3499(19) 0.051(6) Uiso 1 1 d . . . . .
H1B H 0.421(6) 0.611(2) 0.400(2) 0.062(7) Uiso 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
C1 N1 C3 106.62(11) . .
C1 N2 C2 107.44(13) . .
C1 N2 H2A 126.6(19) . .
C2 N2 H2A 125.9(19) . .
N1 C1 N2 110.37(13) . .
N1 C1 C4 125.61(13) . .
N2 C1 C4 124.02(14) . .
C3 C2 N2 106.86(13) . .
C3 C2 H2 126.6 . .
N2 C2 H2 126.6 . .
C2 C3 N1 108.71(13) . .
C2 C3 C5 129.51(16) . .
N1 C3 C5 121.78(14) . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
H1A O1 H1B 103(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3250(17) .
N1 C3 1.382(2) .
N2 C1 1.3501(19) .
N2 C2 1.374(2) .
N2 H2A 0.85(2) .
C1 C4 1.481(2) .
C2 C3 1.354(2) .
C2 H2 0.9500 .
C3 C5 1.496(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
O1 H1A 0.85(3) .
O1 H1B 0.88(3) .
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
O1 H1A O1 0.85(3) 1.94(3) 2.7876(11) 171(2) 2_465
O1 H1B N1 0.88(3) 1.86(3) 2.7254(16) 171(2) .
N2 H2A O1 0.85(2) 1.98(3) 2.8032(16) 165(3) 4_465
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 N1 C1 N2 -0.35(16) . . . .
C3 N1 C1 C4 179.36(13) . . . .
C2 N2 C1 N1 0.32(16) . . . .
C2 N2 C1 C4 -179.39(14) . . . .
C1 N2 C2 C3 -0.16(16) . . . .
N2 C2 C3 N1 -0.05(16) . . . .
N2 C2 C3 C5 179.53(16) . . . .
C1 N1 C3 C2 0.24(16) . . . .
C1 N1 C3 C5 -179.38(14) . . . .
