##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-08-06
_journal_date_accepted     2007-08-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3771
_journal_page_last     o3771
_journal_paper_category     QO
_journal_coeditor_code     HB2505
_publ_contact_author_name     'Edward R. T. Tiekink'
_publ_contact_author_address
;
Department of Chemistry
University of Texas
One UTSA Circle
San Antonio
TX 78249-0698
USA
;
_publ_contact_author_email     edward.tiekink@utsa.edu
_publ_contact_author_fax     '1 210 458 7428'
_publ_contact_author_phone     '1 210 458 5774'
_publ_section_title
;
5-Amino-4-bromo-2-benzofuran-1(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Junyan' .
;
Department of Chemistry
University of Texas at San Antonio
One UTSA Circle
San Antonio
TX 78249-0698
USA
;
    'Johnson, Dave M.'
;
Additional correspondence author, e-mail: dave.johnson@utsa.edu
;
;
Department of Chemistry
University of Texas at San Antonio
One UTSA Circle
San Antonio
TX 78249-0698
USA
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry
University of Texas at San Antonio
One UTSA Circle
San Antonio
TX 78249-0698
USA
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
5-Amino-4-bromo-2-benzofuran-1(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H6 Br N O2'
_chemical_formula_sum     'C8 H6 Br N O2'
_chemical_formula_iupac     'C8 H6 Br N O2'
_chemical_formula_weight     228.05
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     14.353(5)
_cell_length_b     15.090(6)
_cell_length_c     7.5017(18)
_cell_angle_alpha     90
_cell_angle_beta     93.287(10)
_cell_angle_gamma     90
_cell_volume     1622.0(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     7543
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     30.3
_cell_measurement_temperature     153(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.868
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     896
_exptl_absorpt_coefficient_mu     5.021
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.320
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC12κ/SATURN724'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19327
_diffrn_reflns_av_R_equivalents     0.043
_diffrn_reflns_av_sigmaI/netI     0.028
_diffrn_reflns_theta_min     2.7
_diffrn_reflns_theta_max     26.5
_diffrn_reflns_theta_full     26.5
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     '<1'
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3356
_reflns_number_gt     3076
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.065
_refine_ls_R_factor_gt     0.060
_refine_ls_wR_factor_gt     0.155
_refine_ls_wR_factor_ref     0.160
_refine_ls_goodness_of_fit_ref     1.12
_refine_ls_restrained_S_all     1.12
_refine_ls_number_reflns     3356
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0839P)²+5.2755P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.70
_refine_diff_density_min     -0.98
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction     'CrystalClear'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                       'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'SHELXL97'
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
    Br Br1 0.76354(4) 0.14582(4) 0.55865(7) 0.0345(2) Uani d . 1 . .
    Br Br2 0.70712(4) 0.71950(4) -0.02499(8) 0.0423(2) Uani d . 1 . .
    O O1 0.7102(3) 0.4535(3) 0.5012(5) 0.0397(9) Uani d . 1 . .
    O O2 0.5859(3) 0.5183(3) 0.3634(6) 0.0498(11) Uani d . 1 . .
    O O3 0.9376(3) 0.5163(2) -0.1914(6) 0.0428(10) Uani d . 1 . .
    O O4 1.0792(3) 0.5531(3) -0.2830(7) 0.0494(11) Uani d . 1 . .
    N N1 0.5726(4) 0.0837(3) 0.3766(7) 0.0432(12) Uani d . 1 . .
    H H1A 0.5214 0.0596 0.3282 0.052 Uiso calc R 1 . .
    H H1B 0.6183 0.0498 0.4202 0.052 Uiso calc R 1 . .
    N N2 0.8207(4) 0.8909(3) -0.0956(7) 0.0469(12) Uani d . 1 . .
    H H2A 0.7636 0.8882 -0.0588 0.056 Uiso calc R 1 . .
    H H2B 0.8473 0.9427 -0.1108 0.056 Uiso calc R 1 . .
    C C1 0.6238(4) 0.4504(4) 0.4145(7) 0.0372(12) Uani d . 1 . .
    C C2 0.5946(4) 0.3578(3) 0.3977(7) 0.0291(10) Uani d . 1 . .
    C C3 0.5141(3) 0.3199(4) 0.3205(7) 0.0332(11) Uani d . 1 . .
    H H3 0.4644 0.3560 0.2730 0.040 Uiso calc R 1 . .
    C C4 0.5075(4) 0.2281(4) 0.3140(7) 0.0331(11) Uani d . 1 . .
    H H4 0.4525 0.2016 0.2614 0.040 Uiso calc R 1 . .
    C C5 0.5810(4) 0.1726(4) 0.3840(7) 0.0317(11) Uani d . 1 . .
    C C6 0.6623(4) 0.2143(3) 0.4641(7) 0.0285(10) Uani d . 1 . .
    C C7 0.6675(3) 0.3056(4) 0.4689(6) 0.0300(10) Uani d . 1 . .
    C C8 0.7448(4) 0.3646(4) 0.5389(7) 0.0315(11) Uani d . 1 . .
    H H8A 0.7575 0.3558 0.6688 0.038 Uiso calc R 1 . .
    H H8B 0.8027 0.3531 0.4771 0.038 Uiso calc R 1 . .
    C C9 1.0050(4) 0.5772(4) -0.2323(8) 0.0405(13) Uani d . 1 . .
    C C10 0.9705(4) 0.6654(3) -0.2033(7) 0.0322(11) Uani d . 1 . .
    C C11 1.0098(4) 0.7477(4) -0.2266(7) 0.0345(11) Uani d . 1 . .
    H H11 1.0711 0.7528 -0.2669 0.041 Uiso calc R 1 . .
    C C12 0.9592(4) 0.8218(4) -0.1906(8) 0.0377(12) Uani d . 1 . .
    H H12 0.9859 0.8785 -0.2073 0.045 Uiso calc R 1 . .
    C C13 0.8672(4) 0.8159(4) -0.1287(7) 0.0328(11) Uani d . 1 . .
    C C14 0.8289(4) 0.7314(4) -0.1073(7) 0.0314(11) Uani d . 1 . .
    C C15 0.8796(4) 0.6578(4) -0.1420(7) 0.0331(11) Uani d . 1 . .
    C C16 0.8557(4) 0.5614(4) -0.1312(8) 0.0383(12) Uani d . 1 . .
    H H16A 0.8438 0.5443 -0.0071 0.046 Uiso calc R 1 . .
    H H16B 0.7999 0.5473 -0.2096 0.046 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br1 C6 . 1.888(5) ?
    Br2 C14 . 1.895(5) ?
    O1 C1 . 1.367(7) ?
    O1 C8 . 1.452(7) ?
    O2 C1 . 1.212(7) ?
    O3 C9 . 1.381(7) ?
    O3 C16 . 1.453(7) ?
    O4 C9 . 1.208(7) ?
    N1 C5 . 1.348(7) ?
    N1 H1A . 0.8800 ?
    N1 H1B . 0.8800 ?
    N2 C13 . 1.344(7) ?
    N2 H2A . 0.8800 ?
    N2 H2B . 0.8800 ?
    C1 C2 . 1.463(7) ?
    C2 C3 . 1.385(7) ?
    C2 C7 . 1.391(7) ?
    C3 C4 . 1.390(8) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.422(7) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.427(7) ?
    C6 C7 . 1.379(7) ?
    C7 C8 . 1.495(7) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.441(8) ?
    C10 C11 . 1.379(7) ?
    C10 C15 . 1.412(8) ?
    C11 C12 . 1.369(8) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.427(8) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.401(8) ?
    C14 C15 . 1.361(8) ?
    C15 C16 . 1.497(7) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
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
    C1 O1 C8 . . 110.6(4) ?
    C9 O3 C16 . . 110.2(4) ?
    C5 N1 H1A . . 120.0 ?
    C5 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C13 N2 H2A . . 120.0 ?
    C13 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O2 C1 O1 . . 120.0(5) ?
    O2 C1 C2 . . 131.2(5) ?
    O1 C1 C2 . . 108.8(5) ?
    C3 C2 C7 . . 121.2(5) ?
    C3 C2 C1 . . 131.2(5) ?
    C7 C2 C1 . . 107.6(5) ?
    C2 C3 C4 . . 118.6(5) ?
    C2 C3 H3 . . 120.7 ?
    C4 C3 H3 . . 120.7 ?
    C3 C4 C5 . . 121.7(5) ?
    C3 C4 H4 . . 119.1 ?
    C5 C4 H4 . . 119.1 ?
    N1 C5 C4 . . 120.5(5) ?
    N1 C5 C6 . . 121.7(5) ?
    C4 C5 C6 . . 117.8(5) ?
    C7 C6 C5 . . 119.5(5) ?
    C7 C6 Br1 . . 119.8(4) ?
    C5 C6 Br1 . . 120.6(4) ?
    C6 C7 C2 . . 121.1(5) ?
    C6 C7 C8 . . 130.0(5) ?
    C2 C7 C8 . . 108.9(5) ?
    O1 C8 C7 . . 104.1(4) ?
    O1 C8 H8A . . 110.9 ?
    C7 C8 H8A . . 110.9 ?
    O1 C8 H8B . . 110.9 ?
    C7 C8 H8B . . 110.9 ?
    H8A C8 H8B . . 109.0 ?
    O4 C9 O3 . . 120.7(5) ?
    O4 C9 C10 . . 130.0(6) ?
    O3 C9 C10 . . 109.3(5) ?
    C11 C10 C15 . . 120.4(5) ?
    C11 C10 C9 . . 131.7(5) ?
    C15 C10 C9 . . 107.8(5) ?
    C12 C11 C10 . . 119.0(5) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C13 . . 121.7(5) ?
    C11 C12 H12 . . 119.2 ?
    C13 C12 H12 . . 119.2 ?
    N2 C13 C14 . . 122.9(5) ?
    N2 C13 C12 . . 119.1(5) ?
    C14 C13 C12 . . 118.0(5) ?
    C15 C14 C13 . . 120.2(5) ?
    C15 C14 Br2 . . 119.8(4) ?
    C13 C14 Br2 . . 119.9(4) ?
    C14 C15 C10 . . 120.6(5) ?
    C14 C15 C16 . . 131.0(5) ?
    C10 C15 C16 . . 108.3(5) ?
    O3 C16 C15 . . 104.3(4) ?
    O3 C16 H16A . . 110.9 ?
    C15 C16 H16A . . 110.9 ?
    O3 C16 H16B . . 110.9 ?
    C15 C16 H16B . . 110.9 ?
    H16A C16 H16B . . 108.9 ?
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
    C8 O1 C1 O2 . . . . -176.0(5) ?
    C8 O1 C1 C2 . . . . 2.7(6) ?
    O2 C1 C2 C3 . . . . -1.1(11) ?
    O1 C1 C2 C3 . . . . -179.6(5) ?
    O2 C1 C2 C7 . . . . 175.7(6) ?
    O1 C1 C2 C7 . . . . -2.8(6) ?
    C7 C2 C3 C4 . . . . -0.5(8) ?
    C1 C2 C3 C4 . . . . 175.9(5) ?
    C2 C3 C4 C5 . . . . -0.1(8) ?
    C3 C4 C5 N1 . . . . 179.7(5) ?
    C3 C4 C5 C6 . . . . 0.7(7) ?
    N1 C5 C6 C7 . . . . -179.8(5) ?
    C4 C5 C6 C7 . . . . -0.8(7) ?
    N1 C5 C6 Br1 . . . . 1.6(7) ?
    C4 C5 C6 Br1 . . . . -179.5(4) ?
    C5 C6 C7 C2 . . . . 0.3(7) ?
    Br1 C6 C7 C2 . . . . 179.0(4) ?
    C5 C6 C7 C8 . . . . -177.9(5) ?
    Br1 C6 C7 C8 . . . . 0.7(7) ?
    C3 C2 C7 C6 . . . . 0.4(8) ?
    C1 C2 C7 C6 . . . . -176.8(5) ?
    C3 C2 C7 C8 . . . . 179.0(5) ?
    C1 C2 C7 C8 . . . . 1.8(6) ?
    C1 O1 C8 C7 . . . . -1.5(5) ?
    C6 C7 C8 O1 . . . . 178.2(5) ?
    C2 C7 C8 O1 . . . . -0.2(5) ?
    C16 O3 C9 O4 . . . . 179.1(6) ?
    C16 O3 C9 C10 . . . . -0.7(6) ?
    O4 C9 C10 C11 . . . . 1.2(11) ?
    O3 C9 C10 C11 . . . . -179.0(6) ?
    O4 C9 C10 C15 . . . . -179.5(6) ?
    O3 C9 C10 C15 . . . . 0.3(6) ?
    C15 C10 C11 C12 . . . . -0.5(8) ?
    C9 C10 C11 C12 . . . . 178.8(6) ?
    C10 C11 C12 C13 . . . . 0.4(8) ?
    C11 C12 C13 N2 . . . . -179.9(5) ?
    C11 C12 C13 C14 . . . . -0.8(8) ?
    N2 C13 C14 C15 . . . . -179.7(5) ?
    C12 C13 C14 C15 . . . . 1.1(8) ?
    N2 C13 C14 Br2 . . . . -1.0(7) ?
    C12 C13 C14 Br2 . . . . 179.9(4) ?
    C13 C14 C15 C10 . . . . -1.2(8) ?
    Br2 C14 C15 C10 . . . . -180.0(4) ?
    C13 C14 C15 C16 . . . . -179.7(5) ?
    Br2 C14 C15 C16 . . . . 1.6(8) ?
    C11 C10 C15 C14 . . . . 0.9(8) ?
    C9 C10 C15 C14 . . . . -178.6(5) ?
    C11 C10 C15 C16 . . . . 179.6(5) ?
    C9 C10 C15 C16 . . . . 0.2(6) ?
    C9 O3 C16 C15 . . . . 0.8(6) ?
    C14 C15 C16 O3 . . . . 178.0(5) ?
    C10 C15 C16 O3 . . . . -0.6(6) ?
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 H1A O2 2_645 0.88 2.14 2.987(7) 162 y
    N2 H2B O4 2_754 0.88 2.15 3.006(7) 164 y
    N1 H1B Br1 1_555 0.88 2.70 3.135(6) 112 y
    N2 H2A Br2 1_555 0.88 2.69 3.119(5) 111 y
    N2 H2A O1 4_575 0.88 2.56 2.948(7) 108 y
    C8 H8A Br1 4_566 0.99 2.92 3.895(5) 168 y
    C12 H12 O3 2_754 0.95 2.49 3.427(7) 169 y
