#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210539.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_2210539
loop_
_publ_author_name
'Liang, Zu-Pei'
'Li, Jian'
_publ_section_title
;
 2-(4-Hydroxyphenyl)isoindoline-1,3-dione
;
_journal_coeditor_code           CI2156
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4436
_journal_page_last               o4437
_journal_paper_doi               10.1107/S1600536806035963
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H9 N O3'
_chemical_formula_moiety         'C14 H9 N O3'
_chemical_formula_sum            'C14 H9 N O3'
_chemical_formula_weight         239.22
_chemical_name_systematic
;
2-(4-hydroxyphenyl)isoindoline-1,3-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.524(3)
_cell_length_b                   7.7133(19)
_cell_length_c                   24.890(6)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.42
_cell_measurement_theta_min      2.41
_cell_volume                     2212.4(10)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11576
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.161
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0426
_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)+(0.0843P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1300
_reflns_number_total             2265
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2156.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2210539
_cod_database_fobs_code          2210539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.77183(15) -0.0250(2) 0.58590(6) 0.0590(5) Uani d . 1
O O2 0.44736(14) 0.3092(2) 0.60449(6) 0.0530(5) Uani d . 1
O O3 0.66570(16) 0.0333(2) 0.82916(6) 0.0594(6) Uani d . 1
H H3 0.6211 -0.0403 0.8409 0.089 Uiso calc R 1
N N1 0.60792(15) 0.1299(2) 0.60963(7) 0.0350(5) Uani d . 1
C C1 0.6885(2) 0.0607(3) 0.57329(8) 0.0376(6) Uani d . 1
C C2 0.64933(18) 0.1141(3) 0.51912(8) 0.0342(5) Uani d . 1
C C3 0.6961(2) 0.0796(3) 0.46923(9) 0.0435(6) Uani d . 1
H H3A 0.7620 0.0111 0.4656 0.052 Uiso calc R 1
C C4 0.6416(2) 0.1502(3) 0.42493(9) 0.0470(6) Uani d . 1
H H4 0.6718 0.1302 0.3908 0.056 Uiso calc R 1
C C5 0.5424(2) 0.2506(3) 0.43065(9) 0.0467(6) Uani d . 1
H H5 0.5070 0.2971 0.4003 0.056 Uiso calc R 1
C C6 0.49514(19) 0.2827(3) 0.48108(9) 0.0425(6) Uani d . 1
H H6 0.4280 0.3484 0.4850 0.051 Uiso calc R 1
C C7 0.55114(18) 0.2139(3) 0.52476(8) 0.0344(5) Uani d . 1
C C8 0.52461(19) 0.2288(3) 0.58295(9) 0.0358(5) Uani d . 1
C C9 0.61755(19) 0.1118(3) 0.66682(8) 0.0348(5) Uani d . 1
C C10 0.53462(19) 0.0211(3) 0.69535(8) 0.0428(6) Uani d . 1
H H10 0.4697 -0.0226 0.6778 0.051 Uiso calc R 1
C C11 0.54767(19) -0.0049(3) 0.74989(9) 0.0451(6) Uani d . 1
H H11 0.4914 -0.0653 0.7690 0.054 Uiso calc R 1
C C12 0.6442(2) 0.0587(3) 0.77598(8) 0.0389(6) Uani d . 1
C C13 0.7264(2) 0.1509(3) 0.74748(9) 0.0473(6) Uani d . 1
H H13 0.7915 0.1945 0.7650 0.057 Uiso calc R 1
C C14 0.7123(2) 0.1786(3) 0.69306(9) 0.0437(6) Uani d . 1
H H14 0.7670 0.2427 0.6741 0.052 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
C12 O3 H3 109.5
C8 N1 C1 110.94(18)
C8 N1 C9 125.40(18)
C1 N1 C9 123.47(18)
O1 C1 N1 124.6(2)
O1 C1 C2 129.2(2)
N1 C1 C2 106.22(18)
C7 C2 C3 121.4(2)
C7 C2 C1 108.28(17)
C3 C2 C1 130.3(2)
C2 C3 C4 117.8(2)
C2 C3 H3A 121.1
C4 C3 H3A 121.1
C3 C4 C5 120.8(2)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 120.9(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 117.6(2)
C7 C6 H6 121.2
C5 C6 H6 121.2
C6 C7 C2 121.5(2)
C6 C7 C8 130.3(2)
C2 C7 C8 108.20(18)
O2 C8 N1 125.2(2)
O2 C8 C7 128.6(2)
N1 C8 C7 106.27(18)
C14 C9 C10 119.7(2)
C14 C9 N1 119.81(19)
C10 C9 N1 120.4(2)
C11 C10 C9 120.3(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 C10 119.9(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
O3 C12 C11 123.6(2)
O3 C12 C13 116.7(2)
C11 C12 C13 119.7(2)
C12 C13 C14 120.2(2)
C12 C13 H13 119.9
C14 C13 H13 119.9
C9 C14 C13 120.2(2)
C9 C14 H14 119.9
C13 C14 H14 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.207(3)
O2 C8 1.210(2)
O3 C12 1.361(2)
O3 H3 0.82
N1 C8 1.394(3)
N1 C1 1.402(3)
N1 C9 1.435(3)
C1 C2 1.480(3)
C2 C7 1.376(3)
C2 C3 1.379(3)
C3 C4 1.381(3)
C3 H3A 0.93
C4 C5 1.389(3)
C4 H4 0.93
C5 C6 1.390(3)
C5 H5 0.93
C6 C7 1.371(3)
C6 H6 0.93
C7 C8 1.485(3)
C9 C14 1.372(3)
C9 C10 1.381(3)
C10 C11 1.381(3)
C10 H10 0.93
C11 C12 1.379(3)
C11 H11 0.93
C12 C13 1.380(3)
C13 C14 1.381(3)
C13 H13 0.93
C14 H14 0.93
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 O2 3_646 0.82 1.95 2.723(2) 156
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 177.4(2)
C9 N1 C1 O1 2.2(3)
C8 N1 C1 C2 -2.7(2)
C9 N1 C1 C2 -177.85(18)
O1 C1 C2 C7 -178.8(2)
N1 C1 C2 C7 1.3(2)
O1 C1 C2 C3 0.7(4)
N1 C1 C2 C3 -179.2(2)
C7 C2 C3 C4 0.7(3)
C1 C2 C3 C4 -178.7(2)
C2 C3 C4 C5 -0.8(3)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C7 1.0(3)
C5 C6 C7 C2 -1.1(3)
C5 C6 C7 C8 178.1(2)
C3 C2 C7 C6 0.3(3)
C1 C2 C7 C6 179.82(19)
C3 C2 C7 C8 -179.08(19)
C1 C2 C7 C8 0.4(2)
C1 N1 C8 O2 -177.0(2)
C9 N1 C8 O2 -2.0(3)
C1 N1 C8 C7 3.0(2)
C9 N1 C8 C7 177.99(18)
C6 C7 C8 O2 -1.4(4)
C2 C7 C8 O2 177.9(2)
C6 C7 C8 N1 178.6(2)
C2 C7 C8 N1 -2.1(2)
C8 N1 C9 C14 -113.4(2)
C1 N1 C9 C14 61.0(3)
C8 N1 C9 C10 69.3(3)
C1 N1 C9 C10 -116.2(2)
C14 C9 C10 C11 -1.1(3)
N1 C9 C10 C11 176.2(2)
C9 C10 C11 C12 -0.4(4)
C10 C11 C12 O3 -177.5(2)
C10 C11 C12 C13 1.2(4)
O3 C12 C13 C14 178.4(2)
C11 C12 C13 C14 -0.3(4)
C10 C9 C14 C13 1.9(4)
N1 C9 C14 C13 -175.3(2)
C12 C13 C14 C9 -1.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 221039
