##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_I
_audit_creation_method     SHELXL-2014/6
_journal_date_recd_electronic     2016-12-15
_journal_date_accepted     2017-02-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      3
_journal_page_first     372
_journal_page_last     374
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017002079
_journal_coeditor_code     HB7643
_publ_contact_author_name     'Christopher S. Frampton'
_publ_contact_author_address
;
Wolfson Centre for Materials Processing
Brunel University London
Kingston Lane
Uxbridge
UB8 3PH
UK
;
_publ_contact_author_email     'chris.frampton@brunel.ac.uk'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '01895 265337'
_publ_section_title
;
Crystal structure of 1-methylimidazole 3-oxide monohydrate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Frampton, Christopher S.' .
;
Wolfson Centre for Materials Processing
Brunel University London
Kingston Lane
Uxbridge
UB8 3PH
UK
;
    'Murray, James I.' .
;
Department of Chemistry
South Kensington Campus
Imperial College London
London
SW7 2AZ
UK
;
    'Spivey, Alan C.' .
;
Department of Chemistry
South Kensington Campus
Imperial College London
London
SW7 2AZ
UK
;
_publ_section_synopsis
;
1-Methylimidazole 3-N-oxide (NMI-O) crystallizes as a
monohydrate, in the monoclinic space group P2₁ with Z' = 2
(molecules A and B). The imidazole rings display a planar
geometry  and are linked in the crystal structure into infinite zigzag strands
of ...NMI-O(A)...OH₂...NMI-O(B)...OH₂... units by O---H...O
hydrogen bonds. These chains propagate along the b-axis direction of
the unit cell.
;
_database_code_depnum_ccdc_archive
;
1509924
;
_chemical_name_systematic
;
1-Methylimidazole 3-N-oxide monohydrate
;
_chemical_name_common
;
Murray N-oxide catalyst
;
_chemical_formula_moiety     'C4 H6 N2 O, H2 O'
_chemical_formula_sum     'C4 H8 N2 O2'
_chemical_formula_iupac     'C4 H6 N2 O, H2 O'
_chemical_formula_weight     116.12
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     7.5941(6)
_cell_length_b     10.0703(6)
_cell_length_c     7.8286(6)
_cell_angle_alpha     90
_cell_angle_beta     112.402(9)
_cell_angle_gamma     90
_cell_volume     553.51(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1007
_cell_measurement_theta_min     6.29
_cell_measurement_theta_max     74.77
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     Lath
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.450
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.050
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     248
_exptl_absorpt_coefficient_mu     0.953
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_shelx_estimated_absorpt_T_min     0.674
_shelx_estimated_absorpt_T_max     0.954
_exptl_absorpt_correction_T_min     0.41933
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type     'Rigaku SuperNova, Dualflex, AtlasS2'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     5.2921
_diffrn_reflns_number     2067
_diffrn_reflns_av_R_equivalents     0.0229
_diffrn_reflns_theta_min     6.114
_diffrn_reflns_theta_max     74.338
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     7
_refine_special_details     ?
_reflns_number_total     1386
_reflns_number_gt     1241
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0461
_refine_ls_R_factor_gt     0.0415
_refine_ls_wR_factor_gt     0.1143
_refine_ls_wR_factor_ref     0.1192
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_restrained_S_all     1.013
_refine_ls_number_reflns     1386
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.206
_refine_diff_density_min     -0.229
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXD2014 (Sheldrick et al., 2001)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al.,
2008)
and publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1A 0.5193(3) 0.2133(2) 0.5360(3) 0.0218(5) Uani d 1 . .
    N N1A 0.3842(3) 0.2757(3) 0.3934(3) 0.0176(6) Uani d 1 . .
    N N2A 0.2057(4) 0.4269(3) 0.2161(4) 0.0189(6) Uani d 1 . .
    C C1A 0.3553(4) 0.4046(3) 0.3747(4) 0.0193(6) Uani d 1 . .
    H H1A 0.4276 0.4707 0.4589 0.023 Uiso calc 1 . .
    C C2A 0.2517(4) 0.2107(3) 0.2439(4) 0.0185(6) Uani d 1 . .
    H H2A 0.2413 0.1176 0.2231 0.022 Uiso calc 1 . .
    C C3A 0.1392(4) 0.3066(3) 0.1325(4) 0.0185(6) Uani d 1 . .
    H H3A 0.0348 0.2931 0.0187 0.022 Uiso calc 1 . .
    C C4A 0.1200(4) 0.5563(3) 0.1484(5) 0.0231(7) Uani d 1 . .
    H H4AA 0.0184 0.5739 0.1936 0.035 Uiso calc 1 . .
    H H4AB 0.0667 0.5562 0.0130 0.035 Uiso calc 1 . .
    H H4AC 0.2176 0.6256 0.1934 0.035 Uiso calc 1 . .
    O O2A 0.7412(3) 0.3868(2) 0.8081(3) 0.0237(5) Uani d 1 . .
    H H2AA 0.675(7) 0.410(6) 0.898(7) 0.063(16) Uiso d 1 . .
    H H2AB 0.669(6) 0.335(5) 0.729(6) 0.039(13) Uiso d 1 . .
    O O1B 0.5360(3) 0.4513(2) 1.0200(3) 0.0226(5) Uani d 1 . .
    N N1B 0.3895(4) 0.5126(3) 0.8873(3) 0.0188(6) Uani d 1 . .
    N N2B 0.2080(4) 0.6632(3) 0.7115(4) 0.0183(6) Uani d 1 . .
    C C1B 0.3733(4) 0.6430(3) 0.8560(4) 0.0203(7) Uani d 1 . .
    H H1B 0.4617 0.7092 0.9231 0.024 Uiso calc 1 . .
    C C2B 0.2336(4) 0.4478(3) 0.7620(4) 0.0201(6) Uani d 1 . .
    H H2B 0.2105 0.3548 0.7544 0.024 Uiso calc 1 . .
    C C3B 0.1191(4) 0.5435(3) 0.6509(4) 0.0194(6) Uani d 1 . .
    H H3B 0.0007 0.5300 0.5510 0.023 Uiso calc 1 . .
    C C4B 0.1431(4) 0.7915(3) 0.6217(5) 0.0222(7) Uani d 1 . .
    H H4BA 0.1842 0.8624 0.7144 0.033 Uiso calc 1 . .
    H H4BB 0.0038 0.7916 0.5622 0.033 Uiso calc 1 . .
    H H4BC 0.1978 0.8065 0.5284 0.033 Uiso calc 1 . .
    O O2B 0.7272(3) 0.6268(2) 1.2987(3) 0.0242(6) Uani d 1 . .
    H H2BA 0.663(6) 0.585(5) 1.205(5) 0.023(10) Uiso d 1 . .
    H H2BB 0.638(7) 0.648(6) 1.351(7) 0.057(15) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1A N1A . 1.350(3) ?
    N1A C1A . 1.315(4) ?
    N1A C2A . 1.384(4) ?
    N2A C1A . 1.344(4) ?
    N2A C3A . 1.378(4) ?
    N2A C4A . 1.463(4) ?
    C1A H1A . 0.9500 ?
    C2A C3A . 1.362(4) ?
    C2A H2A . 0.9500 ?
    C3A H3A . 0.9500 ?
    C4A H4AA . 0.9800 ?
    C4A H4AB . 0.9800 ?
    C4A H4AC . 0.9800 ?
    O2A H2AA . 1.03(6) ?
    O2A H2AB . 0.83(5) ?
    O1B N1B . 1.348(3) ?
    N1B C1B . 1.332(4) ?
    N1B C2B . 1.380(4) ?
    N2B C1B . 1.348(4) ?
    N2B C3B . 1.374(4) ?
    N2B C4B . 1.464(4) ?
    C1B H1B . 0.9500 ?
    C2B C3B . 1.366(4) ?
    C2B H2B . 0.9500 ?
    C3B H3B . 0.9500 ?
    C4B H4BA . 0.9800 ?
    C4B H4BB . 0.9800 ?
    C4B H4BC . 0.9800 ?
    O2B H2BA . 0.83(4) ?
    O2B H2BB . 0.94(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1A N1A O1A . . 126.5(3) ?
    C1A N1A C2A . . 109.6(3) ?
    O1A N1A C2A . . 123.9(3) ?
    C1A N2A C3A . . 108.6(3) ?
    C1A N2A C4A . . 125.8(3) ?
    C3A N2A C4A . . 125.4(3) ?
    N1A C1A N2A . . 108.3(3) ?
    N1A C1A H1A . . 125.8 ?
    N2A C1A H1A . . 125.8 ?
    C3A C2A N1A . . 106.4(3) ?
    C3A C2A H2A . . 126.8 ?
    N1A C2A H2A . . 126.8 ?
    C2A C3A N2A . . 107.0(3) ?
    C2A C3A H3A . . 126.5 ?
    N2A C3A H3A . . 126.5 ?
    N2A C4A H4AA . . 109.5 ?
    N2A C4A H4AB . . 109.5 ?
    H4AA C4A H4AB . . 109.5 ?
    N2A C4A H4AC . . 109.5 ?
    H4AA C4A H4AC . . 109.5 ?
    H4AB C4A H4AC . . 109.5 ?
    H2AA O2A H2AB . . 107(4) ?
    C1B N1B O1B . . 125.7(3) ?
    C1B N1B C2B . . 110.0(3) ?
    O1B N1B C2B . . 124.3(3) ?
    C1B N2B C3B . . 109.6(3) ?
    C1B N2B C4B . . 124.9(3) ?
    C3B N2B C4B . . 125.3(3) ?
    N1B C1B N2B . . 107.1(3) ?
    N1B C1B H1B . . 126.4 ?
    N2B C1B H1B . . 126.4 ?
    C3B C2B N1B . . 106.5(3) ?
    C3B C2B H2B . . 126.7 ?
    N1B C2B H2B . . 126.7 ?
    C2B C3B N2B . . 106.8(3) ?
    C2B C3B H3B . . 126.6 ?
    N2B C3B H3B . . 126.6 ?
    N2B C4B H4BA . . 109.5 ?
    N2B C4B H4BB . . 109.5 ?
    H4BA C4B H4BB . . 109.5 ?
    N2B C4B H4BC . . 109.5 ?
    H4BA C4B H4BC . . 109.5 ?
    H4BB C4B H4BC . . 109.5 ?
    H2BA O2B H2BB . . 103(4) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1A N1A C1A N2A . . . . -178.9(2) ?
    C2A N1A C1A N2A . . . . 0.2(3) ?
    C3A N2A C1A N1A . . . . -0.1(3) ?
    C4A N2A C1A N1A . . . . 176.4(3) ?
    C1A N1A C2A C3A . . . . -0.2(3) ?
    O1A N1A C2A C3A . . . . 179.0(2) ?
    N1A C2A C3A N2A . . . . 0.1(3) ?
    C1A N2A C3A C2A . . . . 0.0(3) ?
    C4A N2A C3A C2A . . . . -176.6(3) ?
    O1B N1B C1B N2B . . . . 179.6(2) ?
    C2B N1B C1B N2B . . . . 0.0(4) ?
    C3B N2B C1B N1B . . . . 0.0(3) ?
    C4B N2B C1B N1B . . . . -174.4(3) ?
    C1B N1B C2B C3B . . . . 0.0(4) ?
    O1B N1B C2B C3B . . . . -179.6(2) ?
    N1B C2B C3B N2B . . . . 0.0(3) ?
    C1B N2B C3B C2B . . . . 0.0(3) ?
    C4B N2B C3B C2B . . . . 174.4(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O2A H2AA O1B . 1.03(6) 1.73(6) 2.752(3) 172(4)
    O2A H2AB O1A . 0.83(5) 1.94(5) 2.773(3) 175(4)
    O2B H2BA O1B . 0.83(4) 1.94(4) 2.752(3) 167(4)
    O2B H2BB O1A 2_657 0.94(5) 1.86(5) 2.790(3) 171(5)
    C1A H1A O1A 2_656 0.95 2.47 3.248(4) 139
    C4A H4AC O1A 2_656 0.98 2.46 3.308(4) 145
    C4B H4BC O1A 2_656 0.98 2.56 3.336(4) 136
    C1B H1B O1B 2_657 0.95 2.48 3.248(4) 138
    C2B H2B O2B 2_647 0.95 2.41 3.298(4) 155
    C4B H4BA O1B 2_657 0.98 2.50 3.345(4) 144
_shelxl_version_number     2014/6
