#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241151.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_2241151
loop_
_publ_author_name
'Krishnaswamy, G.'
'Krishna Murthy, P.'
'Nivedita Desai, R.'
'Suchetan, P. A.'
'Aruna Kumar, D. B.'
_publ_section_title
;
 Crystal structure of 1-(5-bromobenzofuran-2-yl) ethanone oxime
;
_journal_coeditor_code           HB7505
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o773
_journal_page_last               o774
_journal_paper_doi               10.1107/S205698901501751X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H8 Br N O2'
_chemical_formula_moiety         'C10 H8 Br N O2'
_chemical_formula_sum            'C10 H8 Br N O2'
_chemical_formula_weight         254.08
_chemical_name_systematic
;
1-(5-Bromobenzofuran-2-yl) ethanone oxime
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.943(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9548(6)
_cell_length_b                   9.4897(10)
_cell_length_c                   17.2906(19)
_cell_measurement_reflns_used    125
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      3.5
_cell_volume                     969.91(18)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (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      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10152
_diffrn_reflns_theta_full        29.92
_diffrn_reflns_theta_max         29.92
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    4.208
_exptl_absorpt_correction_T_max  0.413
_exptl_absorpt_correction_T_min  0.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.0157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                1937
_reflns_number_total             2766
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7505sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2241151
_cod_database_fobs_code          2241151
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
_atom_site_symmetry_multiplicity
C C8 0.5278(3) -0.2686(2) -0.00305(11) 0.0391(4) Uani d . 1 1
C C1 0.3056(3) 0.0480(2) 0.16815(12) 0.0447(5) Uani d . 1 1
C C2 0.5215(3) 0.0179(2) 0.20434(11) 0.0492(5) Uani d . 1 1
H H2 0.5745 0.0626 0.2509 0.059 Uiso calc R 1 1
C C3 0.6569(3) -0.0767(2) 0.17233(12) 0.0492(5) Uani d . 1 1
H H3 0.8014 -0.0979 0.1961 0.059 Uiso calc R 1 1
C C4 0.5691(3) -0.1394(2) 0.10298(11) 0.0390(4) Uani d . 1 1
C C5 0.3543(3) -0.1120(2) 0.06601(11) 0.0403(4) Uani d . 1 1
C C6 0.2169(3) -0.0159(2) 0.09927(12) 0.0470(5) Uani d . 1 1
H H6 0.0714 0.0043 0.0761 0.056 Uiso calc R 1 1
C C7 0.3324(3) -0.1982(2) -0.00278(12) 0.0437(5) Uani d . 1 1
H H7 0.2065 -0.2041 -0.0401 0.052 Uiso calc R 1 1
C C9 0.6021(3) -0.3724(2) -0.05598(11) 0.0412(4) Uani d . 1 1
C C10 0.4500(4) -0.4102(3) -0.12802(12) 0.0513(5) Uani d . 1 1
H H10A 0.4955 -0.3594 -0.1716 0.077 Uiso calc R 1 1
H H10B 0.2969 -0.3859 -0.1215 0.077 Uiso calc R 1 1
H H10C 0.4598 -0.5096 -0.1373 0.077 Uiso calc R 1 1
N N1 0.7969(3) -0.42793(19) -0.03532(10) 0.0445(4) Uani d . 1 1
O O1 0.6789(2) -0.23533(16) 0.06169(8) 0.0440(3) Uani d . 1 1
O O2 0.8582(2) -0.52765(17) -0.08799(9) 0.0548(4) Uani d . 1 1
H H2A 0.9720 -0.5695 -0.0688 0.082 Uiso calc R 1 1
Br Br1 0.13019(4) 0.18428(3) 0.214769(13) 0.05936(13) Uani d . 1 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'
Br Br -0.2901 2.4595 '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
C7 C8 O1 111.24(18)
C7 C8 C9 132.16(16)
O1 C8 C9 116.56(17)
C6 C1 C2 122.23(19)
C6 C1 Br1 119.44(15)
C2 C1 Br1 118.33(15)
C3 C2 C1 120.75(18)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 117.00(18)
C2 C3 H3 121.5
C4 C3 H3 121.5
O1 C4 C3 125.70(16)
O1 C4 C5 110.89(16)
C3 C4 C5 123.4(2)
C4 C5 C6 119.22(18)
C4 C5 C7 105.18(17)
C6 C5 C7 135.61(16)
C1 C6 C5 117.40(17)
C1 C6 H6 121.3
C5 C6 H6 121.3
C8 C7 C5 107.11(16)
C8 C7 H7 126.4
C5 C7 H7 126.4
N1 C9 C8 115.94(16)
N1 C9 C10 124.7(2)
C8 C9 C10 119.31(17)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 N1 O2 113.35(16)
C4 O1 C8 105.58(15)
N1 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 C7 1.343(3)
C8 O1 1.385(2)
C8 C9 1.449(3)
C1 C6 1.383(3)
C1 C2 1.390(3)
C1 Br1 1.901(2)
C2 C3 1.367(3)
C2 H2 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 O1 1.371(2)
C4 C5 1.384(2)
C5 C6 1.394(3)
C5 C7 1.437(3)
C6 H6 0.9300
C7 H7 0.9300
C9 N1 1.285(3)
C9 C10 1.493(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
N1 O2 1.392(2)
O2 H2A 0.8200
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
O2 H2A N1 3_745 0.82 2.13 2.808(2) 140
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
C6 C1 C2 C3 0.5(3)
Br1 C1 C2 C3 -178.43(16)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 O1 179.3(2)
C2 C3 C4 C5 -0.6(3)
O1 C4 C5 C6 -179.65(18)
C3 C4 C5 C6 0.3(3)
O1 C4 C5 C7 0.2(2)
C3 C4 C5 C7 -179.9(2)
C2 C1 C6 C5 -0.9(3)
Br1 C1 C6 C5 178.09(15)
C4 C5 C6 C1 0.4(3)
C7 C5 C6 C1 -179.3(2)
O1 C8 C7 C5 0.4(2)
C9 C8 C7 C5 178.2(2)
C4 C5 C7 C8 -0.3(2)
C6 C5 C7 C8 179.5(2)
C7 C8 C9 N1 -174.5(2)
O1 C8 C9 N1 3.3(3)
C7 C8 C9 C10 3.9(4)
O1 C8 C9 C10 -178.38(19)
C8 C9 N1 O2 179.41(17)
C10 C9 N1 O2 1.1(3)
C3 C4 O1 C8 -179.9(2)
C5 C4 O1 C8 0.0(2)
C7 C8 O1 C4 -0.3(2)
C9 C8 O1 C4 -178.48(16)
