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#$Date: 2022-03-29 11:00:34 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104917.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_8104917
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 1,2-dimethylimidazole, C5H8N2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              185
_journal_page_last               186
_journal_paper_doi               10.1515/ncrs-2020-0509
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C5 H8 N2'
_chemical_formula_sum            'C5 H8 N2'
_chemical_formula_weight         96.13
_chemical_name_common            1,2-dimethylimidazole
_chemical_name_systematic        1,2-dimethylimidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 99.214(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2492(6)
_cell_length_b                   7.2496(5)
_cell_length_c                   9.2882(7)
_cell_measurement_reflns_used    3764
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.50
_cell_volume                     548.30(7)
_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 0.987
_diffrn_measured_fraction_theta_max 0.990
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4863
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         3.068
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.574
_exptl_crystal_size_min          0.529
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         1348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0477
_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)+(0.0739P)²+0.1806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1256
_reflns_number_total             1348
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL ea084_s in P2(1)/n
    ea084.res
    created by SHELXL-2018/3 at 23:17:14 on 04-Sep-2020
CELL  0.71073    8.2492    7.2496    9.2882    90.000    99.214    90.000
ZERR        4    0.0006    0.0005    0.0007     0.000     0.002     0.000
LATT   1
SYMM     0.50000 - X ,    0.50000 + Y ,    0.50000 - Z
SFAC  C  H  N
UNIT    20   32   8
ACTA NOHKL
BOND $H
CONF
HTAB
TEMP -73

L.S. 10
FMAP 2
PLAN -5

WGHT    0.073900    0.180600
FVAR       1.05373
N1    3    0.384353    0.095217    0.630484    11.00000    0.02806    0.03525 =
         0.02945   -0.00206    0.00334    0.00100
N2    3    0.599539    0.194463    0.784257    11.00000    0.03650    0.03739 =
         0.03495   -0.00158   -0.00008   -0.00329
C1    1    0.500085    0.053722    0.747066    11.00000    0.02863    0.03218 =
         0.03066    0.00077    0.00403    0.00259
C2    1    0.544419    0.331584    0.685958    11.00000    0.04487    0.03020 =
         0.04315   -0.00033    0.01028   -0.00163
AFIX  43
H2    2    0.592303    0.450670    0.685048    11.00000   -1.20000
AFIX   0
C3    1    0.412546    0.273448    0.590700    11.00000    0.03820    0.03712 =
         0.03462    0.00580    0.00793    0.00760
AFIX  43
H3    2    0.352165    0.341689    0.512672    11.00000   -1.20000
AFIX   0
C4    1    0.256499   -0.025538    0.557112    11.00000    0.03393    0.05343 =
         0.04324   -0.01139    0.00156   -0.00710
AFIX 137
H4A   2    0.306764   -0.126763    0.509961    11.00000   -1.50000
H4B   2    0.183489    0.044761    0.483286    11.00000   -1.50000
H4C   2    0.193048   -0.076021    0.628621    11.00000   -1.50000
AFIX   0
C5    1    0.511490   -0.129758    0.819832    11.00000    0.04495    0.03816 =
         0.05515    0.01386    0.00874    0.00528
AFIX 137
H5A   2    0.554805   -0.220360    0.757511    11.00000   -1.50000
H5B   2    0.402101   -0.168322    0.836368    11.00000   -1.50000
H5C   2    0.585072   -0.121420    0.913535    11.00000   -1.50000
AFIX   0
HKLF 4




REM  ea084_s in P2(1)/n
REM wR2 = 0.1400, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0477 for 1256 Fo > 4sig(Fo) and 0.0501 for all 1348 data
REM 66 parameters refined using 0 restraints

END  
     
WGHT      0.0739      0.1806 

REM Instructions for potential hydrogen bonds
EQIV $1 x-1/2, -y+1/2, z-1/2
HTAB C4 N2_$1

REM Highest difference peak  0.257,  deepest hole -0.171,  1-sigma level  0.038
Q1    1   0.4562 -0.1341  0.9063  11.00000  0.05    0.26
Q2    1   0.5077  0.2969  0.6089  11.00000  0.05    0.24
Q3    1   0.4427  0.0619  0.6824  11.00000  0.05    0.23
Q4    1   0.4540  0.3228  0.6600  11.00000  0.05    0.22
Q5    1   0.4289 -0.2216  0.7538  11.00000  0.05    0.19
;
_cod_data_source_file            suppl_j_ncrs-2020-0509_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104917
_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.
;
_iucr_geom_bonds_special_details
;                                                              
Cg(1) is the centroid of atoms N1--C1--N2--C2--C3.            
;
loop_
_space_group_symop_operation_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_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 0.38435(12) 0.09522(14) 0.63048(10) 0.0311(3) Uani 1 1 d . . . . .
N2 N 0.59954(13) 0.19446(15) 0.78426(11) 0.0369(3) Uani 1 1 d . . . . .
C1 C 0.50008(13) 0.05372(16) 0.74707(12) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.54442(17) 0.33158(18) 0.68596(14) 0.0391(3) Uani 1 1 d . . . . .
H2 H 0.592303 0.450670 0.685048 0.047 Uiso 1 1 calc R U . . .
C3 C 0.41255(16) 0.27345(18) 0.59070(13) 0.0364(3) Uani 1 1 d . . . . .
H3 H 0.352165 0.341689 0.512672 0.044 Uiso 1 1 calc R U . . .
C4 C 0.25650(16) -0.0255(2) 0.55711(15) 0.0440(4) Uani 1 1 d . . . . .
H4A H 0.306764 -0.126763 0.509961 0.066 Uiso 1 1 calc R U . . .
H4B H 0.183489 0.044761 0.483286 0.066 Uiso 1 1 calc R U . . .
H4C H 0.193048 -0.076021 0.628621 0.066 Uiso 1 1 calc R U . . .
C5 C 0.51149(18) -0.1298(2) 0.81983(17) 0.0460(4) Uani 1 1 d . . . . .
H5A H 0.554805 -0.220360 0.757511 0.069 Uiso 1 1 calc R U . . .
H5B H 0.402101 -0.168322 0.836368 0.069 Uiso 1 1 calc R U . . .
H5C H 0.585072 -0.121420 0.913535 0.069 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0281(5) 0.0353(6) 0.0295(5) -0.0021(4) 0.0033(4) 0.0010(4)
N2 0.0365(6) 0.0374(6) 0.0349(5) -0.0016(4) -0.0001(4) -0.0033(4)
C1 0.0286(5) 0.0322(6) 0.0307(6) 0.0008(4) 0.0040(4) 0.0026(4)
C2 0.0449(7) 0.0302(6) 0.0432(7) -0.0003(5) 0.0103(5) -0.0016(5)
C3 0.0382(6) 0.0371(6) 0.0346(6) 0.0058(5) 0.0079(5) 0.0076(5)
C4 0.0339(6) 0.0534(8) 0.0432(7) -0.0114(6) 0.0016(5) -0.0071(6)
C5 0.0449(7) 0.0382(7) 0.0552(8) 0.0139(6) 0.0087(6) 0.0053(6)
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'
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 107.17(10) . .
C1 N1 C4 127.24(11) . .
C3 N1 C4 125.57(11) . .
C1 N2 C2 105.02(11) . .
N2 C1 N1 111.45(11) . .
N2 C1 C5 125.49(11) . .
N1 C1 C5 123.06(11) . .
C3 C2 N2 110.72(12) . .
C3 C2 H2 124.6 . .
N2 C2 H2 124.6 . .
C2 C3 N1 105.65(11) . .
C2 C3 H3 127.2 . .
N1 C3 H3 127.2 . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C1 C5 H5A 109.5 . .
C1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3577(14) .
N1 C3 1.3739(17) .
N1 C4 1.4536(15) .
N2 C1 1.3201(16) .
N2 C2 1.3768(17) .
C1 C5 1.4882(17) .
C2 C3 1.3549(19) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
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
C4 H4A <i>C<i>~g~(1) 0.98 2.73 3.5435(15) 141 3_656
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
C2 N2 C1 N1 -0.25(13) . . . .
C2 N2 C1 C5 178.87(12) . . . .
C3 N1 C1 N2 0.27(13) . . . .
C4 N1 C1 N2 178.65(11) . . . .
C3 N1 C1 C5 -178.87(11) . . . .
C4 N1 C1 C5 -0.49(18) . . . .
C1 N2 C2 C3 0.14(14) . . . .
N2 C2 C3 N1 0.02(14) . . . .
C1 N1 C3 C2 -0.17(13) . . . .
C4 N1 C3 C2 -178.58(11) . . . .
