#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223681.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_2223681
loop_
_publ_author_name
'Devarajegowda, H. C.'
'Madhura, V.'
'Palakshamurthy, B. S.'
'Jeyaseelan, S.'
'Kulkarni, Manohar V.'
_publ_section_title
;
 1,3-Bis(hydroxymethyl)benzimidazolin-2-one
;
_journal_coeditor_code           CI2925
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2735
_journal_paper_doi               10.1107/S1600536809040963
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H10 N2 O3'
_chemical_formula_moiety         'C9 H10 N2 O3'
_chemical_formula_sum            'C9 H10 N2 O3'
_chemical_formula_weight         194.19
_chemical_melting_point          433
_chemical_name_systematic
;
1,3-Bis(hydroxymethyl)benzimidazolin-2-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.216(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   13.5515(14)
_cell_length_b                   11.0848(12)
_cell_length_c                   17.6253(19)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.32
_cell_volume                     2640.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13521
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+1.5821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2395
_reflns_number_total             2684
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2925.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223681
_cod_database_fobs_code          2223681
loop_
_symmetry_equiv_pos_as_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.36019(9) 0.44213(11) 0.19000(7) 0.0555(3) Uani d . 1 . .
H H1A 0.4009 0.3984 0.2131 0.083 Uiso d R 1 . .
O O2 0.51268(9) 0.85515(11) -0.04107(7) 0.0560(3) Uani d . 1 . .
H H2A 0.4597 0.8565 -0.0667 0.084 Uiso d R 1 . .
O O3 0.32846(8) 0.69395(11) 0.07135(7) 0.0525(3) Uani d . 1 . .
N N1 0.44553(9) 0.54147(11) 0.09507(7) 0.0390(3) Uani d . 1 . .
N N2 0.49663(9) 0.72131(11) 0.06132(7) 0.0420(3) Uani d . 1 . .
C C1 0.61458(12) 0.44272(15) 0.11034(9) 0.0469(4) Uani d . 1 . .
H H1 0.5932 0.3665 0.1238 0.056 Uiso calc R 1 . .
C C2 0.71420(13) 0.46756(18) 0.10526(10) 0.0568(5) Uani d . 1 . .
H H2 0.7604 0.4063 0.1146 0.068 Uiso calc R 1 . .
C C3 0.74639(13) 0.5819(2) 0.08647(10) 0.0582(5) Uani d . 1 . .
H H3 0.8138 0.5963 0.0847 0.070 Uiso calc R 1 . .
C C4 0.67978(12) 0.67501(17) 0.07028(9) 0.0499(4) Uani d . 1 . .
H H4 0.7012 0.7516 0.0576 0.060 Uiso calc R 1 . .
C C5 0.58057(11) 0.64950(13) 0.07380(8) 0.0388(3) Uani d . 1 . .
C C6 0.54853(11) 0.53545(13) 0.09463(8) 0.0372(3) Uani d . 1 . .
C C7 0.41401(11) 0.65604(14) 0.07545(8) 0.0398(3) Uani d . 1 . .
C C8 0.49544(14) 0.84582(14) 0.03582(10) 0.0511(4) Uani d . 1 . .
H H8A 0.4317 0.8813 0.0440 0.061 Uiso calc R 1 . .
H H8B 0.5458 0.8909 0.0658 0.061 Uiso calc R 1 . .
C C9 0.37880(12) 0.44495(14) 0.11304(9) 0.0456(4) Uani d . 1 . .
H H9A 0.3166 0.4549 0.0827 0.055 Uiso calc R 1 . .
H H9B 0.4072 0.3684 0.0993 0.055 Uiso calc R 1 . .
O O4 0.5000 0.27510(13) 0.2500 0.0467(4) Uani d S 1 . .
O O5 0.33811(9) 0.12882(13) 0.36950(7) 0.0628(4) Uani d . 1 . .
H H5A 0.2848 0.1462 0.3858 0.094 Uiso d R 1 . .
N N3 0.42148(9) 0.09011(11) 0.26254(7) 0.0396(3) Uani d . 1 . .
C C10 0.45046(15) -0.24348(15) 0.25741(9) 0.0553(5) Uani d . 1 . .
H H10 0.4179 -0.3167 0.2617 0.066 Uiso calc R 1 . .
C C11 0.39872(13) -0.13699(15) 0.26601(9) 0.0487(4) Uani d . 1 . .
H H11 0.3325 -0.1370 0.2765 0.058 Uiso calc R 1 . .
C C12 0.45049(11) -0.03066(13) 0.25817(8) 0.0385(3) Uani d . 1 . .
C C13 0.5000 0.16353(19) 0.2500 0.0379(4) Uani d S 1 . .
C C14 0.32941(11) 0.13248(16) 0.28957(9) 0.0468(4) Uani d . 1 . .
H H14A 0.3162 0.2143 0.2722 0.056 Uiso calc R 1 . .
H H14B 0.2752 0.0814 0.2701 0.056 Uiso calc R 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'
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
C9 O1 H1A . . 109.4 ?
C8 O2 H2A . . 109.5 ?
C7 N1 C6 . . 109.53(12) ?
C7 N1 C9 . . 123.27(13) ?
C6 N1 C9 . . 127.20(12) ?
C7 N2 C5 . . 109.76(12) ?
C7 N2 C8 . . 124.58(14) ?
C5 N2 C8 . . 125.66(13) ?
C6 C1 C2 . . 117.39(16) ?
C6 C1 H1 . . 121.3 ?
C2 C1 H1 . . 121.3 ?
C1 C2 C3 . . 121.40(16) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 121.16(16) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 117.36(16) ?
C5 C4 H4 . . 121.3 ?
C3 C4 H4 . . 121.3 ?
C4 C5 N2 . . 131.54(15) ?
C4 C5 C6 . . 121.39(14) ?
N2 C5 C6 . . 107.05(13) ?
C1 C6 C5 . . 121.26(14) ?
C1 C6 N1 . . 131.97(14) ?
C5 C6 N1 . . 106.76(12) ?
O3 C7 N2 . . 125.99(14) ?
O3 C7 N1 . . 127.14(14) ?
N2 C7 N1 . . 106.87(12) ?
O2 C8 N2 . . 111.86(14) ?
O2 C8 H8A . . 109.2 ?
N2 C8 H8A . . 109.2 ?
O2 C8 H8B . . 109.2 ?
N2 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
O1 C9 N1 . . 112.84(13) ?
O1 C9 H9A . . 109.0 ?
N1 C9 H9A . . 109.0 ?
O1 C9 H9B . . 109.0 ?
N1 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C14 O5 H5A . . 109.5 ?
C13 N3 C12 . . 109.55(12) ?
C13 N3 C14 . . 124.00(13) ?
C12 N3 C14 . . 125.57(13) ?
C10 C10 C11 2_655 . 121.66(10) ?
C10 C10 H10 2_655 . 119.2 ?
C11 C10 H10 . . 119.2 ?
C12 C11 C10 . . 116.74(16) ?
C12 C11 H11 . . 121.6 ?
C10 C11 H11 . . 121.6 ?
C11 C12 C12 . 2_655 121.59(10) ?
C11 C12 N3 . . 131.53(14) ?
C12 C12 N3 2_655 . 106.88(8) ?
O4 C13 N3 . . 126.43(9) ?
O4 C13 N3 . 2_655 126.43(9) ?
N3 C13 N3 . 2_655 107.14(18) ?
O5 C14 N3 . . 108.05(13) ?
O5 C14 H14A . . 110.1 ?
N3 C14 H14A . . 110.1 ?
O5 C14 H14B . . 110.1 ?
N3 C14 H14B . . 110.1 ?
H14A C14 H14B . . 108.4 ?
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
O1 C9 . 1.3981(19) ?
O1 H1A . 0.82 ?
O2 C8 . 1.396(2) ?
O2 H2A . 0.82 ?
O3 C7 . 1.2304(18) ?
N1 C7 . 1.3759(19) ?
N1 C6 . 1.3980(19) ?
N1 C9 . 1.4509(19) ?
N2 C7 . 1.371(2) ?
N2 C5 . 1.3925(19) ?
N2 C8 . 1.451(2) ?
C1 C6 . 1.378(2) ?
C1 C2 . 1.387(2) ?
C1 H1 . 0.93 ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.395(2) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
O4 C13 . 1.237(3) ?
O5 C14 . 1.406(2) ?
O5 H5A . 0.82 ?
N3 C13 . 1.3704(17) ?
N3 C12 . 1.3990(19) ?
N3 C14 . 1.4462(19) ?
C10 C10 2_655 1.387(4) ?
C10 C11 . 1.387(3) ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.93 ?
C12 C12 2_655 1.393(3) ?
C13 N3 2_655 1.3704(17) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
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 H1A O4 . 0.82 1.99 2.8003(16) 169
O2 H2A O5 6_565 0.82 1.93 2.7503(18) 176
O5 H5A O3 4_545 0.82 1.84 2.6551(17) 175
C3 H3 O2 7_665 0.93 2.58 3.489(2) 164
C14 H14B O1 4_545 0.97 2.54 3.364(2) 143
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
C6 C1 C2 C3 . . . . 1.2(3) ?
C1 C2 C3 C4 . . . . -1.5(3) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C3 C4 C5 N2 . . . . 179.76(16) ?
C3 C4 C5 C6 . . . . 1.6(2) ?
C7 N2 C5 C4 . . . . -177.04(16) ?
C8 N2 C5 C4 . . . . 4.1(3) ?
C7 N2 C5 C6 . . . . 1.36(16) ?
C8 N2 C5 C6 . . . . -177.55(14) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
C2 C1 C6 N1 . . . . -179.32(15) ?
C4 C5 C6 C1 . . . . -1.9(2) ?
N2 C5 C6 C1 . . . . 179.46(14) ?
C4 C5 C6 N1 . . . . 177.94(13) ?
N2 C5 C6 N1 . . . . -0.65(16) ?
C7 N1 C6 C1 . . . . 179.60(16) ?
C9 N1 C6 C1 . . . . -0.3(3) ?
C7 N1 C6 C5 . . . . -0.27(16) ?
C9 N1 C6 C5 . . . . 179.81(14) ?
C5 N2 C7 O3 . . . . 178.30(15) ?
C8 N2 C7 O3 . . . . -2.8(2) ?
C5 N2 C7 N1 . . . . -1.52(16) ?
C8 N2 C7 N1 . . . . 177.40(14) ?
C6 N1 C7 O3 . . . . -178.71(15) ?
C9 N1 C7 O3 . . . . 1.2(2) ?
C6 N1 C7 N2 . . . . 1.10(16) ?
C9 N1 C7 N2 . . . . -178.97(13) ?
C7 N2 C8 O2 . . . . -105.28(17) ?
C5 N2 C8 O2 . . . . 73.5(2) ?
C7 N1 C9 O1 . . . . -88.27(17) ?
C6 N1 C9 O1 . . . . 91.64(17) ?
C10 C10 C11 C12 2_655 . . . 0.8(3) ?
C10 C11 C12 C12 . . . 2_655 0.5(3) ?
C10 C11 C12 N3 . . . . 179.38(15) ?
C13 N3 C12 C11 . . . . -179.51(14) ?
C14 N3 C12 C11 . . . . 10.9(3) ?
C13 N3 C12 C12 . . . 2_655 -0.50(18) ?
C14 N3 C12 C12 . . . 2_655 -170.07(15) ?
C12 N3 C13 O4 . . . . -179.81(7) ?
C14 N3 C13 O4 . . . . -10.04(16) ?
C12 N3 C13 N3 . . . 2_655 0.19(7) ?
C14 N3 C13 N3 . . . 2_655 169.96(16) ?
C13 N3 C14 O5 . . . . -89.75(16) ?
C12 N3 C14 O5 . . . . 78.38(18) ?
