#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231276.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_2231276
loop_
_publ_author_name
'Betz, Richard'
'Gerber, Thomas'
'Hosten, Eric'
'Schalekamp, Henk'
_publ_section_title
;
 2-Hydroxy-N-(2-hydroxyethyl)benzamide
;
_journal_coeditor_code           QM2017
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2117
_journal_paper_doi               10.1107/S1600536811029175
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 N O3'
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_name_systematic
;
2-Hydroxy-N-(2-hydroxyethyl)benzamide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.682(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5852(5)
_cell_length_b                   12.1716(7)
_cell_length_c                   9.1113(4)
_cell_measurement_reflns_used    3230
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.63
_cell_volume                     858.04(8)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7333
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                1561
_reflns_number_total             2063
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            qm2017.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231276
_cod_database_fobs_code          2231276
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
O O1 0.12173(15) 0.16491(9) 0.50668(12) 0.0345(3) Uani d . 1 1
O O2 0.30777(16) 0.07953(10) 0.78461(13) 0.0385(3) Uani d . 1 1
H H82 0.234(3) 0.1262(18) 0.709(3) 0.059(6) Uiso d . 1 1
O O3 -0.01603(15) 0.12074(9) -0.05944(13) 0.0320(3) Uani d . 1 1
H H83 0.031(3) 0.188(2) -0.050(3) 0.064(7) Uiso d . 1 1
N N1 0.05024(16) 0.06865(10) 0.27683(15) 0.0265(3) Uani d . 1 1
H H71 0.055(2) 0.0087(15) 0.226(2) 0.040(5) Uiso d . 1 1
C C1 0.14136(19) 0.08091(11) 0.43613(17) 0.0245(3) Uani d . 1 1
C C2 0.26991(18) -0.00403(11) 0.53026(17) 0.0240(3) Uani d . 1 1
C C3 0.35056(19) 0.00197(12) 0.70163(17) 0.0272(3) Uani d . 1 1
C C4 0.4777(2) -0.07369(13) 0.79138(19) 0.0325(4) Uani d . 1 1
H H4 0.5303 -0.0700 0.9069 0.039 Uiso calc R 1 1
C C5 0.5277(2) -0.15370(13) 0.7143(2) 0.0341(4) Uani d . 1 1
H H5 0.6155 -0.2045 0.7768 0.041 Uiso calc R 1 1
C C6 0.4508(2) -0.16085(12) 0.54536(19) 0.0317(4) Uani d . 1 1
H H6 0.4856 -0.2162 0.4923 0.038 Uiso calc R 1 1
C C7 0.3235(2) -0.08696(12) 0.45544(18) 0.0283(3) Uani d . 1 1
H H7 0.2708 -0.0923 0.3400 0.034 Uiso calc R 1 1
C C8 -0.0703(2) 0.15326(12) 0.17864(18) 0.0280(3) Uani d . 1 1
H H8A -0.0098 0.2248 0.1976 0.034 Uiso calc R 1 1
H H8B -0.1655 0.1603 0.2118 0.034 Uiso calc R 1 1
C C9 -0.1441(2) 0.12462(13) -0.00029(18) 0.0310(3) Uani d . 1 1
H H9A -0.2021 0.0523 -0.0179 0.037 Uiso calc R 1 1
H H9B -0.2324 0.1799 -0.0633 0.037 Uiso calc R 1 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 0.0439(7) 0.0284(5) 0.0239(6) 0.0066(5) 0.0079(5) -0.0031(4)
O2 0.0498(8) 0.0381(6) 0.0212(6) 0.0072(6) 0.0093(5) -0.0028(5)
O3 0.0442(7) 0.0261(5) 0.0238(5) -0.0026(5) 0.0131(5) -0.0015(4)
N1 0.0295(7) 0.0247(6) 0.0211(6) 0.0024(5) 0.0068(5) -0.0005(5)
C1 0.0269(8) 0.0251(7) 0.0214(7) -0.0029(6) 0.0103(6) -0.0004(6)
C2 0.0243(7) 0.0233(7) 0.0221(7) -0.0043(6) 0.0078(6) -0.0001(5)
C3 0.0297(8) 0.0274(7) 0.0222(7) -0.0051(6) 0.0092(6) -0.0009(6)
C4 0.0325(9) 0.0352(8) 0.0224(7) -0.0026(7) 0.0049(6) 0.0048(6)
C5 0.0284(8) 0.0325(8) 0.0341(9) 0.0014(6) 0.0067(7) 0.0075(7)
C6 0.0320(9) 0.0275(7) 0.0335(8) 0.0018(6) 0.0122(7) -0.0013(6)
C7 0.0303(8) 0.0278(7) 0.0233(7) -0.0021(6) 0.0082(6) -0.0016(6)
C8 0.0299(8) 0.0271(7) 0.0240(7) 0.0047(6) 0.0089(6) 0.0026(6)
C9 0.0293(8) 0.0315(8) 0.0231(7) 0.0030(6) 0.0029(6) 0.0005(6)
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
C3 O2 H82 106.2(13)
C9 O3 H83 109.0(13)
C1 N1 C8 121.13(12)
C1 N1 H71 122.0(12)
C8 N1 H71 116.8(12)
O1 C1 N1 120.34(13)
O1 C1 C2 120.13(13)
N1 C1 C2 119.51(12)
C7 C2 C3 117.96(13)
C7 C2 C1 122.61(13)
C3 C2 C1 119.30(12)
O2 C3 C4 117.80(13)
O2 C3 C2 122.16(13)
C4 C3 C2 120.04(13)
C5 C4 C3 120.54(14)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.44(14)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 119.45(14)
C7 C6 H6 120.3
C5 C6 H6 120.3
C6 C7 C2 121.56(14)
C6 C7 H7 119.2
C2 C7 H7 119.2
N1 C8 C9 110.64(12)
N1 C8 H8A 109.5
C9 C8 H8A 109.5
N1 C8 H8B 109.5
C9 C8 H8B 109.5
H8A C8 H8B 108.1
O3 C9 C8 112.70(13)
O3 C9 H9A 109.1
C8 C9 H9A 109.1
O3 C9 H9B 109.1
C8 C9 H9B 109.1
H9A C9 H9B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2573(17)
O2 C3 1.3559(18)
O2 H82 0.90(2)
O3 C9 1.4193(19)
O3 H83 0.90(2)
N1 C1 1.3255(18)
N1 C8 1.4594(18)
N1 H71 0.874(18)
C1 C2 1.484(2)
C2 C7 1.402(2)
C2 C3 1.4092(19)
C3 C4 1.391(2)
C4 C5 1.374(2)
C4 H4 0.9500
C5 C6 1.390(2)
C5 H5 0.9500
C6 C7 1.378(2)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.512(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
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
O2 H82 O1 . 0.90(2) 1.73(2) 2.5570(15) 150(2)
O3 H83 O1 4_565 0.90(2) 1.93(2) 2.8197(15) 168.3(19)
N1 H71 O3 3 0.874(18) 2.113(19) 2.9697(16) 166.6(17)
C4 H4 O2 3_657 0.95 2.54 3.4864(19) 173.3
C7 H7 O3 3 0.95 2.57 3.4496(19) 154.6
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
C8 N1 C1 O1 2.0(2)
C8 N1 C1 C2 -176.53(12)
O1 C1 C2 C7 -166.39(14)
N1 C1 C2 C7 12.2(2)
O1 C1 C2 C3 9.4(2)
N1 C1 C2 C3 -172.01(13)
C7 C2 C3 O2 179.76(13)
C1 C2 C3 O2 3.8(2)
C7 C2 C3 C4 -0.7(2)
C1 C2 C3 C4 -176.74(13)
O2 C3 C4 C5 -179.44(14)
C2 C3 C4 C5 1.0(2)
C3 C4 C5 C6 -0.7(2)
C4 C5 C6 C7 0.0(2)
C5 C6 C7 C2 0.3(2)
C3 C2 C7 C6 0.1(2)
C1 C2 C7 C6 175.95(13)
C1 N1 C8 C9 174.38(13)
N1 C8 C9 O3 -63.35(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 81622
