#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231145.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231145
loop_
_publ_author_name
'Chelghoum, Meryem'
'Bahnous, Mebarek'
'Bouacida, Sofiane'
'Roisnel, Thierry'
'Belfaitah, Ali'
_publ_section_title
;
 2-Hydroxymethyl-1,3-dimethylimidazolium iodide
;
_journal_coeditor_code           HG5062
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1890
_journal_paper_doi               10.1107/S1600536811025700
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H11 N2 O +, I -'
_chemical_formula_moiety         'C6 H11 N2 O +, I -'
_chemical_formula_sum            'C6 H11 I N2 O'
_chemical_formula_weight         254.07
_chemical_name_systematic
;
2-Hydroxymethyl-1,3-dimethylimidazolium iodide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3428(3)
_cell_length_b                   7.2186(3)
_cell_length_c                   16.8870(8)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.42
_cell_volume                     893.79(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4200
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    3.525
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.536
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.3175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0628
_reflns_number_gt                1463
_reflns_number_total             2035
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231145
_cod_database_fobs_code          2231145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I I1 0.80624(2) 0.74882(2) 0.413580(10) 0.02430(8) Uani d . 1 1
C C1 0.6996(5) 0.2724(3) 0.20049(17) 0.0284(6) Uani d . 1 1
H H1A 0.8326 0.2864 0.2033 0.043 Uiso calc R 1 1
H H1B 0.6438 0.3775 0.1716 0.043 Uiso calc R 1 1
H H1C 0.6663 0.157 0.1728 0.043 Uiso calc R 1 1
N N2 0.6343(3) 0.2668(2) 0.28084(14) 0.0204(5) Uani d . 1 1
C C3 0.4551(4) 0.2855(3) 0.29967(18) 0.0251(6) Uani d . 1 1
H H3 0.3528 0.3011 0.2634 0.03 Uiso calc R 1 1
C C4 0.4528(4) 0.2773(3) 0.37988(17) 0.0232(6) Uani d . 1 1
H H4 0.3482 0.2865 0.4104 0.028 Uiso calc R 1 1
N N5 0.6304(3) 0.2533(2) 0.40871(13) 0.0195(5) Uani d . 1 1
C C6 0.6882(4) 0.2431(3) 0.49319(18) 0.0271(6) Uani d . 1 1
H H6A 0.7534 0.1265 0.5038 0.041 Uiso calc R 1 1
H H6B 0.5807 0.2483 0.5251 0.041 Uiso calc R 1 1
H H6C 0.7689 0.3475 0.5071 0.041 Uiso calc R 1 1
C C7 0.7404(4) 0.2472(3) 0.34775(16) 0.0192(5) Uani d . 1 1
C C8 0.9437(4) 0.2288(3) 0.35238(19) 0.0254(6) Uani d . 1 1
H H8A 0.9867 0.2055 0.4081 0.03 Uiso calc R 1 1
H H8B 0.9789 0.1212 0.3202 0.03 Uiso calc R 1 1
O O9 1.0295(3) 0.3905(2) 0.32453(12) 0.0305(4) Uani d . 1 1
H H9 0.9902 0.4838 0.348 0.046 Uiso calc R 1 1
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N2 C1 H1A 109.5
N2 C1 H1B 109.5
H1A C1 H1B 109.5
N2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 N2 C3 109.5(2)
C7 N2 C1 125.3(3)
C3 N2 C1 125.2(3)
C4 C3 N2 106.9(3)
C4 C3 H3 126.6
N2 C3 H3 126.6
C3 C4 N5 107.2(3)
C3 C4 H4 126.4
N5 C4 H4 126.4
C7 N5 C4 109.3(2)
C7 N5 C6 126.1(3)
C4 N5 C6 124.6(2)
N5 C6 H6A 109.5
N5 C6 H6B 109.5
H6A C6 H6B 109.5
N5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N5 C7 N2 107.2(3)
N5 C7 C8 127.0(3)
N2 C7 C8 125.7(3)
O9 C8 C7 111.6(2)
O9 C8 H8A 109.3
C7 C8 H8A 109.3
O9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108
C8 O9 H9 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.464(4)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
N2 C7 1.345(3)
N2 C3 1.376(4)
C3 C4 1.357(4)
C3 H3 0.95
C4 N5 1.379(4)
C4 H4 0.95
N5 C7 1.343(3)
N5 C6 1.468(4)
C6 H6A 0.98
C6 H6B 0.98
C6 H6C 0.98
C7 C8 1.497(4)
C8 O9 1.419(3)
C8 H8A 0.99
C8 H8B 0.99
O9 H9 0.84
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_publ_flag
O9 H9 I1 0.84 2.62 3.4504(18) 169 yes
C1 H1A O9 0.98 2.55 3.230(4) 126 yes
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
C7 N2 C3 C4 0.1(3)
C1 N2 C3 C4 -178.4(2)
N2 C3 C4 N5 -0.2(3)
C3 C4 N5 C7 0.2(2)
C3 C4 N5 C6 178.15(19)
C4 N5 C7 N2 -0.1(2)
C6 N5 C7 N2 -178.06(18)
C4 N5 C7 C8 178.0(2)
C6 N5 C7 C8 0.1(3)
C3 N2 C7 N5 0.0(2)
C1 N2 C7 N5 178.48(18)
C3 N2 C7 C8 -178.1(2)
C1 N2 C7 C8 0.3(3)
N5 C7 C8 O9 -113.9(3)
N2 C7 C8 O9 63.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656852
