#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239878.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_2239878
loop_
_publ_author_name
'Suchetan, P. A.'
'Naveen, S.'
'Lokanath, N. K.'
'Sreenivasa, S.'
_publ_section_title
;
 Crystal structure of N-(3-hydroxyphenyl)succinimide
;
_journal_coeditor_code           SU2752
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o927
_journal_paper_doi               10.1107/S1600536814016328
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H9 N O3'
_chemical_formula_moiety         'C10 H9 N O3'
_chemical_formula_sum            'C10 H9 N O3'
_chemical_formula_weight         191.18
_chemical_melting_point          393
_chemical_name_common
;
N-(3-Hydroxyphenyl)succinimide
;
_chemical_name_systematic
;
1-(3-Hydroxyphenyl)pyrrolidine-2,5-dione
;
_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                 98.688(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.432(2)
_cell_length_b                   7.6567(14)
_cell_length_c                   10.115(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.0
_cell_measurement_theta_min      3.9
_cell_volume                     875.2(3)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3786
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0440
_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)+(0.0766P)²+0.2946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1207
_reflns_number_total             1234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2752sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239878
_cod_database_fobs_code          2239878
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.91904(12) 0.1492(2) 0.88087(15) 0.0436(5) Uani d . 1.000
O O2 0.56202(12) -0.1251(2) 0.82562(16) 0.0482(5) Uani d . 1.000
O O3 0.92280(13) -0.1661(2) 0.43867(15) 0.0454(5) Uani d . 1.000
N N1 0.74293(13) 0.0058(2) 0.82293(16) 0.0293(5) Uani d . 1.000
C C1 0.74308(15) -0.0001(2) 0.68070(19) 0.0281(6) Uani d . 1.000
C C2 0.83725(16) -0.0782(2) 0.63281(18) 0.0300(6) Uani d . 1.000
C C3 0.83605(17) -0.0861(3) 0.49542(19) 0.0326(6) Uani d . 1.000
C C4 0.74209(18) -0.0147(3) 0.4099(2) 0.0391(7) Uani d . 1.000
C C5 0.64917(18) 0.0627(3) 0.4603(2) 0.0407(7) Uani d . 1.000
C C6 0.64839(17) 0.0704(3) 0.5970(2) 0.0361(6) Uani d . 1.000
C C7 0.65000(16) -0.0592(2) 0.8850(2) 0.0327(6) Uani d . 1.000
C C8 0.68144(17) -0.0292(3) 1.0320(2) 0.0374(7) Uani d . 1.000
C C9 0.80476(18) 0.0493(3) 1.0518(2) 0.0367(6) Uani d . 1.000
C C10 0.83298(16) 0.0764(2) 0.91334(19) 0.0313(6) Uani d . 1.000
H H2 0.90020 -0.12450 0.69140 0.0360 Uiso c R 1.000
H H3 0.978(3) -0.223(5) 0.502(4) 0.088(10) Uiso d . 1.000
H H4 0.74170 -0.01900 0.31800 0.0470 Uiso c R 1.000
H H5 0.58650 0.11000 0.40200 0.0490 Uiso c R 1.000
H H6 0.58570 0.12170 0.63140 0.0430 Uiso c R 1.000
H H8A 0.68090 -0.13840 1.08050 0.0450 Uiso c R 1.000
H H8B 0.62560 0.05040 1.06340 0.0450 Uiso c R 1.000
H H9A 0.80610 0.15940 1.09940 0.0440 Uiso c R 1.000
H H9B 0.86130 -0.02960 1.10190 0.0440 Uiso c R 1.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 O3 H3 112(2) no
C1 N1 C10 124.14(15) no
C7 N1 C10 112.43(16) no
C1 N1 C7 123.43(15) no
N1 C1 C6 118.80(16) no
C2 C1 C6 122.34(18) no
N1 C1 C2 118.85(16) no
C1 C2 C3 118.63(17) no
O3 C3 C4 117.31(17) no
C2 C3 C4 119.80(18) no
O3 C3 C2 122.87(18) no
C3 C4 C5 120.42(19) no
C4 C5 C6 120.57(19) no
C1 C6 C5 118.24(19) no
O2 C7 N1 123.91(18) no
N1 C7 C8 107.82(16) no
O2 C7 C8 128.27(18) no
C7 C8 C9 105.74(16) no
C8 C9 C10 104.97(16) no
O1 C10 C9 127.74(18) no
N1 C10 C9 108.71(16) no
O1 C10 N1 123.55(18) no
C1 C2 H2 121.00 no
C3 C2 H2 121.00 no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C1 C6 H6 121.00 no
C5 C6 H6 121.00 no
C7 C8 H8A 111.00 no
C7 C8 H8B 111.00 no
C9 C8 H8A 111.00 no
C9 C8 H8B 111.00 no
H8A C8 H8B 109.00 no
C8 C9 H9A 111.00 no
C8 C9 H9B 111.00 no
C10 C9 H9A 111.00 no
C10 C9 H9B 111.00 no
H9A C9 H9B 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.218(2) no
O2 C7 1.202(2) no
O3 C3 1.364(3) no
O3 H3 0.94(4) no
N1 C1 1.440(2) no
N1 C7 1.404(2) no
N1 C10 1.380(2) no
C1 C2 1.382(2) no
C1 C6 1.380(3) no
C2 C3 1.389(3) no
C3 C4 1.386(3) no
C4 C5 1.380(3) no
C5 C6 1.385(3) no
C7 C8 1.494(3) no
C8 C9 1.518(3) no
C9 C10 1.498(3) no
C2 H2 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C8 H8A 0.9700 no
C8 H8B 0.9700 no
C9 H9A 0.9700 no
C9 H9B 0.9700 no
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
O3 H3 O1 2_746 0.94(4) 1.82(4) 2.758(2) 175(4)
C8 H8A Cg 4_565 0.97 2.83 3.613(3) 138
C9 H9A Cg 4_565 0.97 2.79 3.579(3) 139
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
_geom_torsion_publ_flag
C7 N1 C1 C2 -125.04(18) no
C10 N1 C1 C2 55.4(2) no
C7 N1 C1 C6 54.1(2) no
C10 N1 C1 C6 -125.46(19) no
C7 N1 C10 C9 3.7(2) no
C1 N1 C10 O1 4.0(3) no
C7 N1 C10 O1 -175.62(16) no
C1 N1 C7 O2 -0.3(3) no
C10 N1 C7 C8 -0.1(2) no
C10 N1 C7 O2 179.37(17) no
C1 N1 C10 C9 -176.69(16) no
C1 N1 C7 C8 -179.75(16) no
C6 C1 C2 C3 -0.2(3) no
N1 C1 C6 C5 -179.51(18) no
N1 C1 C2 C3 178.96(16) no
C2 C1 C6 C5 -0.4(3) no
C1 C2 C3 C4 0.7(3) no
C1 C2 C3 O3 -177.55(17) no
C2 C3 C4 C5 -0.6(3) no
O3 C3 C4 C5 177.7(2) no
C3 C4 C5 C6 0.1(3) no
C4 C5 C6 C1 0.4(3) no
O2 C7 C8 C9 177.14(19) no
N1 C7 C8 C9 -3.4(2) no
C7 C8 C9 C10 5.3(2) no
C8 C9 C10 O1 173.70(18) no
C8 C9 C10 N1 -5.6(2) no
