#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/46/2214697.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_2214697
loop_
_publ_author_name
'Wang, Junyan'
'Johnson, Dave M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 6-Amino-3H-isobenzofuran-1-one
;
_journal_coeditor_code           HB2488
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3634
_journal_page_last               o3634
_journal_paper_doi               10.1107/S1600536807035763
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 N O2'
_chemical_formula_moiety         'C8 H7 N O2'
_chemical_formula_sum            'C8 H7 N O2'
_chemical_formula_weight         149.15
_chemical_name_common            6-aminophthalide
_chemical_name_systematic
;
6-Amino-3H-isobenzofuran-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 99.242(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.396(2)
_cell_length_b                   5.990(2)
_cell_length_c                   14.012(4)
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.7
_cell_volume                     695.5(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku AFC12κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4579
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.042
_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)+(0.0459P)²+0.2023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                1370
_reflns_number_total             1436
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2488.cif
_cod_data_source_block           I
_cod_original_cell_volume        695.5(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214697
_cod_database_fobs_code          2214697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.74553(11) 0.30158(17) 0.91253(7) 0.0408(3) Uani d . 1
O O2 0.71640(11) -0.03455(17) 0.84229(7) 0.0393(3) Uani d . 1
N N1 0.10635(15) 0.3245(3) 0.94360(11) 0.0529(4) Uani d D 1
H H1N 0.0067 0.2770 0.9418 0.079 Uiso d D 1
H H2N 0.1367 0.4437 0.9785 0.079 Uiso d D 1
C C1 0.65841(15) 0.1465(2) 0.88321(9) 0.0321(3) Uani d . 1
C C2 0.58839(16) -0.1970(2) 0.81381(11) 0.0386(3) Uani d . 1
H H2A 0.6135 -0.3405 0.8479 0.046 Uiso calc R 1
H H2B 0.5726 -0.2240 0.7432 0.046 Uiso calc R 1
C C3 0.44184(15) -0.0911(2) 0.84286(9) 0.0301(3) Uani d . 1
C C4 0.28242(16) -0.1620(2) 0.83663(9) 0.0330(3) Uani d . 1
H H4 0.2494 -0.3028 0.8091 0.040 Uiso calc R 1
C C5 0.17340(15) -0.0233(2) 0.87133(9) 0.0337(3) Uani d . 1
H H5 0.0648 -0.0714 0.8677 0.040 Uiso calc R 1
C C6 0.21809(15) 0.1874(2) 0.91198(9) 0.0339(3) Uani d . 1
C C7 0.37826(15) 0.2566(2) 0.91822(9) 0.0318(3) Uani d . 1
H H7 0.4125 0.3972 0.9455 0.038 Uiso calc R 1
C C8 0.48546(14) 0.1144(2) 0.88350(9) 0.0285(3) Uani d . 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 0.0281(5) 0.0427(6) 0.0506(6) -0.0048(4) 0.0037(4) -0.0033(5)
O2 0.0287(5) 0.0412(6) 0.0494(6) 0.0035(4) 0.0102(4) -0.0034(4)
N1 0.0270(6) 0.0604(9) 0.0721(9) 0.0014(6) 0.0100(6) -0.0306(7)
C1 0.0268(6) 0.0359(7) 0.0334(7) 0.0028(5) 0.0044(5) 0.0026(5)
C2 0.0338(7) 0.0351(7) 0.0479(8) 0.0029(5) 0.0094(6) -0.0051(6)
C3 0.0305(7) 0.0299(6) 0.0301(6) 0.0021(5) 0.0055(5) 0.0010(5)
C4 0.0340(7) 0.0307(6) 0.0339(7) -0.0030(5) 0.0037(5) -0.0018(5)
C5 0.0264(6) 0.0399(7) 0.0347(7) -0.0031(5) 0.0049(5) -0.0005(5)
C6 0.0275(6) 0.0406(7) 0.0331(7) 0.0032(5) 0.0035(5) -0.0053(5)
C7 0.0274(6) 0.0339(7) 0.0330(7) 0.0012(5) 0.0018(5) -0.0062(5)
C8 0.0259(6) 0.0315(6) 0.0276(6) 0.0006(5) 0.0024(5) 0.0018(5)
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
C1 O2 C2 110.57(10)
C6 N1 H1N 119.5
C6 N1 H2N 120.9
H1N N1 H2N 118
O1 C1 O2 121.26(12)
O1 C1 C8 130.08(12)
O2 C1 C8 108.67(11)
O2 C2 C3 104.17(11)
O2 C2 H2A 110.9
C3 C2 H2A 110.9
O2 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 108.9
C8 C3 C4 119.09(12)
C8 C3 C2 108.34(11)
C4 C3 C2 132.58(13)
C5 C4 C3 118.60(12)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 122.15(12)
C4 C5 H5 118.9
C6 C5 H5 118.9
N1 C6 C7 120.22(13)
N1 C6 C5 120.95(12)
C7 C6 C5 118.82(12)
C8 C7 C6 118.02(12)
C8 C7 H7 121.0
C6 C7 H7 121.0
C3 C8 C7 123.33(12)
C3 C8 C1 108.25(11)
C7 C8 C1 128.42(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2123(16)
O2 C1 1.3535(17)
O2 C2 1.4570(17)
N1 C6 1.3726(18)
N1 H1N 0.8801
N1 H2N 0.8801
C1 C8 1.4654(17)
C2 C3 1.4976(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C8 1.3808(18)
C3 C4 1.3937(18)
C4 C5 1.3810(19)
C4 H4 0.9500
C5 C6 1.4104(19)
C5 H5 0.9500
C6 C7 1.3965(18)
C7 C8 1.3830(17)
C7 H7 0.9500
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
_geom_hbond_publ_flag
N1 H1N O1 1_455 0.88 2.17 2.9937(19) 156 y
N1 H2N O1 3_667 0.88 2.27 3.134(2) 167 y
C2 H2A O1 1_545 0.99 2.51 3.477(2) 164 y
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
C2 O2 C1 O1 179.64(12)
C2 O2 C1 C8 -0.42(14)
C1 O2 C2 C3 0.01(14)
O2 C2 C3 C8 0.42(14)
O2 C2 C3 C4 -178.97(13)
C8 C3 C4 C5 0.13(19)
C2 C3 C4 C5 179.47(13)
C3 C4 C5 C6 0.5(2)
C4 C5 C6 N1 178.26(14)
C4 C5 C6 C7 -0.7(2)
N1 C6 C7 C8 -178.63(13)
C5 C6 C7 C8 0.33(19)
C4 C3 C8 C7 -0.49(19)
C2 C3 C8 C7 -179.98(12)
C4 C3 C8 C1 178.81(11)
C2 C3 C8 C1 -0.68(14)
C6 C7 C8 C3 0.26(19)
C6 C7 C8 C1 -178.90(12)
O1 C1 C8 C3 -179.37(13)
O2 C1 C8 C3 0.70(14)
O1 C1 C8 C7 -0.1(2)
O2 C1 C8 C7 179.96(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 84519
