#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238151.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_2238151
loop_
_publ_author_name
'Sanders, Marisa B.'
'Farrokh, John C.'
'Hardie, Joseph'
'Chan, Benny C.'
_publ_section_title
;
 (1H-Imidazol-4-yl)methanol
;
_journal_coeditor_code           FJ2622
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1151
_journal_paper_doi               10.1107/S160053681301636X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C4 H6 N2 O'
_chemical_formula_moiety         'C4 H6 N2 O'
_chemical_formula_sum            'C4 H6 N2 O'
_chemical_formula_weight         98.11
_chemical_name_systematic
;
(1H-Imidazol-4-yl)methanol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.1-2'
_cell_angle_alpha                90
_cell_angle_beta                 125.2490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9180(9)
_cell_length_b                   7.1980(5)
_cell_length_c                   11.6509(12)
_cell_measurement_reflns_used    189
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.1727
_cell_measurement_theta_min      3.6153
_cell_volume                     953.20(13)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker Software, 2009)'
_computing_publication_material  'enCIFer (Allen et al. 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_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            5389
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0511P)²+0.6749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                1086
_reflns_number_total             1158
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL c2c in C2/c
CELL 0.71073 13.9180 7.1980 11.6509 90.000 125.249 90.000
ZERR 8.00 0.0009 0.0005 0.0012 0.000 0.001 0.000
LATT 7
SYMM -x, y, -z+1/2
SFAC C  H  N  O
UNIT 32  48  16  8
L.S. 4
ACTA 50
BOND $H
FMAP 2
PLAN -5
TEMP -173
WGHT      0.0511      0.6749
FVAR       0.23022
O1    4    0.396789    0.037524    1.062916    11.00000    0.01593    0.01770 =
         0.01824    0.00317    0.00921    0.00348
AFIX 147
H1    2    0.452753   -0.037417    1.092916    11.00000   -1.50000
AFIX   0
N1    3    0.434714    0.233675    0.850462    11.00000    0.01635    0.01727 =
         0.01889    0.00079    0.01029    0.00195
N2    3    0.279127    0.411157    0.711670    11.00000    0.01646    0.01636 =
         0.01773    0.00242    0.00839    0.00275
AFIX  43
H2    2    0.224334    0.473158    0.636741    11.00000   -1.20000
AFIX   0
C1    1    0.437075    0.223066    1.067697    11.00000    0.01969    0.01794 =
         0.01505   -0.00120    0.00799    0.00091
AFIX  23
H1A   2    0.524113    0.224484    1.124603    11.00000   -1.20000
H1B   2    0.411790    0.306689    1.113055    11.00000   -1.20000
AFIX   0
C2    1    0.388494    0.291177    0.922955    11.00000    0.01581    0.01405 =
         0.01658   -0.00155    0.00875   -0.00079
C3    1    0.365921    0.309714    0.724078    11.00000    0.01803    0.01677 =
         0.01918    0.00064    0.01122    0.00058
AFIX  43
H3    2    0.376585    0.294462    0.651108    11.00000   -1.20000
AFIX   0
C4    1    0.291799    0.400117    0.837511    11.00000    0.01827    0.01651 =
         0.01934   -0.00005    0.01128    0.00204
AFIX  43
H4    2    0.243258    0.456664    0.860487    11.00000   -1.20000
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM  c2c in C2/c
REM R1 =  0.0349 for   1086 Fo > 4sig(Fo)  and  0.0368 for all   1158 data
REM     65 parameters refined using      0 restraints
END
WGHT      0.0511      0.6749
REM Highest difference peak  0.370,  deepest hole -0.272,  1-sigma level  0.046
Q1    1   0.4139  0.2586  0.9937  11.00000  0.05    0.37
Q2    1   0.3307  0.3186  0.8794  11.00000  0.05    0.28
Q3    1   0.4126  0.2574  0.8901  11.00000  0.05    0.27
Q4    1   0.4013  0.2621  0.7863  11.00000  0.05    0.23
Q5    1   0.2885  0.4207  0.7763  11.00000  0.05    0.23
;
_cod_data_source_file            fj2622.cif
_cod_data_source_block           I
_cod_database_code               2238151
_cod_database_fobs_code          2238151
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
O O1 0.39678(6) 0.03753(10) 1.06291(7) 0.0178(2) Uani d . 1
H H1 0.4528 -0.0374 1.093 0.027 Uiso calc R 1
N N1 0.43471(7) 0.23365(12) 0.85046(9) 0.0176(2) Uani d . 1
N N2 0.27914(7) 0.41114(12) 0.71171(9) 0.0178(2) Uani d . 1
H H2 0.2243 0.4731 0.6368 0.021 Uiso calc R 1
C C1 0.43706(9) 0.22305(14) 1.06767(10) 0.0189(2) Uani d . 1
H H1A 0.5241 0.2245 1.1246 0.023 Uiso calc R 1
H H1B 0.4118 0.3067 1.113 0.023 Uiso calc R 1
C C2 0.38850(8) 0.29121(13) 0.92295(10) 0.0160(2) Uani d . 1
C C3 0.36594(9) 0.30971(14) 0.72413(11) 0.0178(2) Uani d . 1
H H3 0.3766 0.2945 0.6512 0.021 Uiso calc R 1
C C4 0.29183(9) 0.40012(14) 0.83752(11) 0.0179(2) Uani d . 1
H H4 0.2433 0.4567 0.8605 0.021 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0161(4) 0.0178(4) 0.0184(4) 0.0035(3) 0.0093(3) 0.0032(3)
N1 0.0164(4) 0.0173(4) 0.0191(4) 0.0018(3) 0.0103(4) 0.0007(3)
N2 0.0165(4) 0.0164(4) 0.0178(4) 0.0027(3) 0.0083(3) 0.0024(3)
C1 0.0197(5) 0.0181(5) 0.0154(5) 0.0009(4) 0.0081(4) -0.0012(4)
C2 0.0159(5) 0.0140(4) 0.0169(5) -0.0009(3) 0.0088(4) -0.0016(3)
C3 0.0182(5) 0.0168(5) 0.0193(5) 0.0005(4) 0.0113(4) 0.0005(4)
C4 0.0184(5) 0.0165(5) 0.0196(5) 0.0019(4) 0.0114(4) -0.0001(4)
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_site_symmetry_3
C1 O1 H1 109.5
C3 N1 C2 105.14(8)
C3 N2 C4 107.41(8)
C3 N2 H2 126.3
C4 N2 H2 126.3
O1 C1 C2 110.48(8)
O1 C1 H1A 109.6
C2 C1 H1A 109.6
O1 C1 H1B 109.6
C2 C1 H1B 109.6
H1A C1 H1B 108.1
C4 C2 N1 109.58(9)
C4 C2 C1 128.67(9)
N1 C2 C1 121.54(9)
N1 C3 N2 111.82(9)
N1 C3 H3 124.1
N2 C3 H3 124.1
C2 C4 N2 106.04(8)
C2 C4 H4 127.0
N2 C4 H4 127.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4369(12)
O1 H1 0.84
N1 C3 1.3251(13)
N1 C2 1.3877(12)
N2 C3 1.3459(13)
N2 C4 1.3738(13)
N2 H2 0.88
C1 C2 1.4917(13)
C1 H1A 0.99
C1 H1B 0.99
C2 C4 1.3674(14)
C3 H3 0.95
C4 H4 0.95
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
O1 H1 N1 5_657 0.84 1.92 2.7563(13) 172
N2 H2 O1 7_557 0.88 1.99 2.8315(11) 161
C4 H4 O1 4_556 0.95 2.57 3.4574(17) 155
