#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215131.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_2215131
loop_
_publ_author_name
'Wang, Junyan'
'Johnson, Dave M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 5-Amino-4-bromo-2-benzofuran-1(3H)-one
;
_journal_coeditor_code           HB2505
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3771
_journal_page_last               o3771
_journal_paper_doi               10.1107/S1600536807039049
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H6 Br N O2'
_chemical_formula_moiety         'C8 H6 Br N O2'
_chemical_formula_sum            'C8 H6 Br N O2'
_chemical_formula_weight         228.05
_chemical_name_systematic
;
5-Amino-4-bromo-2-benzofuran-1(3H)-one
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 93.287(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.353(5)
_cell_length_b                   15.090(6)
_cell_length_c                   7.5017(18)
_cell_measurement_reflns_used    7543
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.7
_cell_volume                     1622.1(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19327
_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    5.021
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.70
_refine_diff_density_min         -0.98
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.060
_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)+(0.0839P)²+5.2755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.155
_refine_ls_wR_factor_ref         0.160
_reflns_number_gt                3076
_reflns_number_total             3356
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2505.cif
_cod_data_source_block           I
_cod_original_cell_volume        1622.0(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215131
_cod_database_fobs_code          2215131
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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 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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13298092
2 PubChem 139072932
