#------------------------------------------------------------------------------
#$Date: 2018-12-22 05:37:55 +0200 (Sat, 22 Dec 2018) $
#$Revision: 212747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/03/1550385.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_1550385
loop_
_publ_author_name
'Hmissa, Taha'
'Mathivathanan, Logesh'
'Thompson, Alexander P.'
'Mirjafari, Arsalan'
_publ_section_title
;
 1-Methyl-1H-imidazol-3-ium methanesulfonate
;
_journal_coeditor_code           BV4023
_journal_issue                   12
_journal_name_full               IUCrData
_journal_page_first              x181781
_journal_paper_doi               10.1107/S2414314618017819
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C4 H7 N2 +, C H3 O3 S -'
_chemical_formula_moiety         'C4 H7 N2 +, C H3 O3 S -'
_chemical_formula_sum            'C5 H10 N2 O3 S'
_chemical_formula_weight         178.21
_chemical_name_systematic
;
1-Methyl-1H-imidazol-3-ium methanesulfonate
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1891(5)
_cell_length_b                   7.4627(4)
_cell_length_c                   11.4884(6)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      3.33
_cell_volume                     812.02(7)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      230(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11035
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_min         3.330
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0399P)²+0.3268P] where
 P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1827
_reflns_number_total             2011
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bv4023sup1.cif
_cod_data_source_block           I
_cod_database_code               1550385
_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   0.817
_shelx_estimated_absorpt_t_max   0.881
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_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_occupancy
S S1 0.67678(3) 0.74219(4) 0.90924(3) 0.02711(11) Uani d 1
O O1 0.72814(12) 0.64890(15) 0.82397(10) 0.0424(3) Uani d 1
O O2 0.58946(10) 0.62642(13) 0.95480(8) 0.0354(2) Uani d 1
O O3 0.78655(11) 0.83115(16) 1.01095(10) 0.0468(3) Uani d 1
N N1 0.38601(11) 0.26564(14) 0.59635(10) 0.0283(2) Uani d 1
N N2 0.43894(12) 0.37124(16) 0.78128(11) 0.0384(3) Uani d 1
H H2 0.483452 0.427925 0.850900 0.046 Uiso calc 1
C C1 0.47811(14) 0.36423(18) 0.68438(13) 0.0349(3) Uani d 1
H H1 0.558245 0.420035 0.678699 0.042 Uiso calc 1
C C2 0.28337(14) 0.2092(2) 0.63836(13) 0.0347(3) Uani d 1
H H2A 0.204560 0.137987 0.594256 0.042 Uiso calc 1
C C3 0.31699(16) 0.2752(2) 0.75517(14) 0.0408(3) Uani d 1
H H3 0.266479 0.258443 0.808246 0.049 Uiso calc 1
C C4 0.38835(18) 0.2315(2) 0.47203(14) 0.0456(4) Uani d 1
H H4A 0.362591 0.107785 0.448925 0.068 Uiso calc 1
H H4B 0.482460 0.253917 0.472837 0.068 Uiso calc 1
H H4C 0.321550 0.310260 0.411695 0.068 Uiso calc 1
C C5 0.56302(18) 0.9098(3) 0.81923(19) 0.0552(4) Uani d 1
H H5A 0.484569 0.854603 0.752852 0.083 Uiso calc 1
H H5B 0.614304 0.987198 0.782942 0.083 Uiso calc 1
H H5C 0.527445 0.980152 0.872276 0.083 Uiso calc 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 0.0000 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'
S S 0.1246 0.1234 '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
O1 S1 O2 112.08(6)
O1 S1 C5 105.57(8)
O2 S1 C5 105.88(7)
O3 S1 O1 113.73(7)
O3 S1 O2 111.83(6)
O3 S1 C5 107.10(9)
C1 N1 C2 108.71(11)
C1 N1 C4 125.66(12)
C2 N1 C4 125.53(12)
C1 N2 H2 125.4
C1 N2 C3 109.15(12)
C3 N2 H2 125.4
N1 C1 H1 125.7
N2 C1 N1 108.58(12)
N2 C1 H1 125.7
N1 C2 H2A 126.5
C3 C2 N1 106.92(12)
C3 C2 H2A 126.5
N2 C3 H3 126.7
C2 C3 N2 106.63(13)
C2 C3 H3 126.7
N1 C4 H4A 109.5
N1 C4 H4B 109.5
N1 C4 H4C 109.5
H4A C4 H4B 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
S1 C5 H5A 109.5
S1 C5 H5B 109.5
S1 C5 H5C 109.5
H5A C5 H5B 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
S1 O1 1.4478(10)
S1 O2 1.4680(9)
S1 O3 1.4468(10)
S1 C5 1.7590(16)
N1 C1 1.3210(17)
N1 C2 1.3699(17)
N1 C4 1.4596(17)
N2 H2 0.8700
N2 C1 1.3149(19)
N2 C3 1.369(2)
C1 H1 0.9400
C2 H2A 0.9400
C2 C3 1.350(2)
C3 H3 0.9400
C4 H4A 0.9700
C4 H4B 0.9700
C4 H4C 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C5 H5C 0.9700
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
N2 H2 O2 0.87 1.96 2.775(2) 155.7 yes

_cod_database_fobs_code 1550385
